Alkyl sulfonyl sulfonamides

ABSTRACT

This invention relates to alkyl sulfonyl sulfonamides which are useful as herbicides and plant growth regulants.

RELATED APPLICATION

This is a division of application Ser. No. 511,471, filed July 8, 1983,now U.S. Pat. No. 4,543,120 which is in turn a continuation-in-part ofmy copending application U.S. Ser. No. 407,645, filed Aug. 12, 1982 nowabandoned.

BACKGROUND OF THE INVENTION

This invention relates to novel alkyl sulfonyl sulfonamides. Thecompounds of this invention and their agriculturally suitable salts, areuseful as agricultural chemicals, e.g. plant growth regulants andherbicides.

Netherlands Patent No. 121,788, published Sept. 15, 1966, discloses thepreparation of compounds of the following Formula and their use asgeneral or selective herbicides: ##STR1## wherein R₁ and R₂ mayindependently be alkyl of 1-4 carbon atoms; and

R₃ and R₄ may independently be hydrogen, chlorine or alkyl of 1-4 carbonatoms.

U.S. Pat. No. 3,637,366 discloses compounds having the formula: ##STR2##wherein R₁ is hydrogen or lower saturated aliphatic acyl and

R₂ is hydrogen, 2-pyrimidinyl, pyridyl, amidino, acetyl or carbamoyl.

The disclosed compounds are said to provide control of crabgrass, cress,endive, clover and Poa annua.

French Patent No. 1,468,747 discloses the following para-substitutedphenylsulfonamides as being useful as antidiabetic agents: ##STR3##wherein R=H, halogen, CF₃ or alkyl.

Logemann et al., Chem. Ab., 53, 18052g (1959), disclose a number ofsulfonamides, including uracil derivatives and those having the formula:##STR4## wherein R is butyl, phenyl or ##STR5## and R₁ is hydrogen ormethyl.

When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g),the compounds in which R is butyl and phenyl were most potent. Theothers were of low potency or inactive.

Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 591633 e] describes the synthesis ofN-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide:##STR6##

U.S. Pat. No. 4,127,405 teaches compounds which are useful forcontrolling weeds in wheat having the formula ##STR7## wherein R is##STR8## R₁ is ##STR9## R₃ and R₆ are independently hydrogen, fluorine,chlorine, bromine, iodine, alkyl of 1-4 carbon atoms, alkoxy of 1-4carbon atoms, nitro, trifluoromethyl, cyano, CH₃ S(O)_(n) -- or CH₃ CH₂S(O)_(n) --;

R₄ is hydrogen, fluorine, chlorine, bromine or methyl;

R₅ is hydrogen, fluorine, chlorine, bromine, methyl or methoxy;

R₇ is hydrogen, fluorine, chlorine, bromine, alkyl of 1-2 carbon atomsor alkoxy of 1-2 carbon atom;

R₈ is hydrogen, methyl, chlorine or bromine;

R₉ and R₁₀ are independently hydrogen, methyl, chlorine or bromine;

W and Q are independently oxygen or sulfur;

n is 0, 1 or 2;

X is hydrogen, chlorine, bromine, methyl, ethyl, alkoxy of 1-3 carbonatoms, trifluoromethyl, CH₃ S-- or CH₃ OCH₂ --; and

Z is methyl or methoxy;

or their agriculturally suitable salts; provided that:

(a) when R₅ is other than hydrogen, at least one of R₃, R₄, R₆ and R₇ isother than hydrogen and at least two of R₃, R₄, R₆ and R₇ must behydrogen;

(b) when R₅ is hydrogen and all of R₃, R₄, R₆ and R₇ are other thanhydrogen, then all of R₃, R₄, R₆ and R₇ must be either chlorine ormethyl; and

(c) when R₃ and R₇ are both hydrogen, at least one of R₄, R₅ or R₆ mustbe hydrogen.

In EPO Publication No. 0030433, herbicidal sulfonylureas including aderivative of 4-amino heterocycle are taught.

In EPO Publication No. 0035893, published Sept. 16, 1981, the followingcompounds are taught. ##STR10## wherein R₁ is R₃ S(O)_(n) where R₃ is C₃-C₄ alkyl, C₃ -C₄ alkenyl, cyclopropylmethyl or cyclopentyl;

R₂ is H, F, Cl, Br, CH₃, OCH₃, CF₃, NO₂, CN or NH₂ ;

n is 0, 1 or 2;

W is 0 or S;

Z is CH or N;

X is CH₃, C₂ H₅, CH₃ O, C₂ H₅ O or CH₂ OCH₃ ; and

Y is CH₃ or CH₃ O;

and their agriculturally suitable salts; with the proviso that when R₂is CN, then R₂ is not meta to R₁ ; and further provided that when W isS, then n is 0 or 2.

The presence of undesired vegetation causes substantial damage to usefulcrops, especially agricultural products that satisfy man's basic foodand fiber needs, such as cotton, rice, corn, wheat, and the like. Thecurrent population explosion and concomitant world food and fibershortage demand improvements in the efficiency of producing these crops.Prevention or minimizing the loss of a portion of such valuable crops bykilling, or inhibiting the growth of undesired vegetation is one way ofimproving this efficiency. A wide variety of materials useful forkilling, or inhibiting (controlling) the growth of undesired vegetationis available; such materials are commonly referred to as herbicides. Theneed still exists however, for more effective herbicides.

SUMMARY OF THE INVENTION

This invention relates to compounds of Formula I, agriculturallysuitable compositions containing them, and their method-of-use asgeneral or selective pre-emergent or post-emergent herbicides or plantgrowth regulants. ##STR11## wherein R₁ is S(O)_(n) R₃ ;

R₂ is H, F, Cl, Br, CH₃, OCH₃, CF₃ or NO₂ ;

R₃ is C₁ -C₄ alkyl, C₃ -C₄ alkenyl or cyclopropylmethyl;

n is 0, 1 or 2;

X is CH₃, C₂ H₅, CH₃ O, C₂ H₅ O, CH₂ OCH₃ or Cl;

Y is Cl, F, Br, NH₂, NHCH₃ or N(CH₃)₂ ; and

Z is CH or N;

and their agriculturally suitable salts; provided that

(1) when R₃ is C₃ -C₄ alkenyl, then Y is NH₂, NHCH₃ or N(CH₃)₂ ;

(2) when R₃ is C₁ -C₂ alkyl and Y is Cl or Br, then X is other than CH₃or OCH₃ ;

(3) when R₃ is C₁ -C₃ alkyl and Y is NH₂ or NHCH₃, then X is other thanCl, CH₂ CH₃ or CH₂ OCH₃ ;

(4) when Y is Cl, F or Br, then Z is CH and X is CH₃, OCH₃ or OCH₂ CH₃ ;and

(5) when X is Cl, then Z is CH and Y is N(CH₃)₂.

Preferred for reasons of their higher herbicidal activity, greater plantgrowth regulant activity and/or more favorble ease of synthesis are:

(1) Compounds of Formula I where n is 2.

(2) Compounds of Preferred 1 where R₂ is H, Cl, CH₃, CH₃ O or CF₃.

(3) Compounds of Preferred 2 where X is CH₃ or OCH₃.

(4) Compounds of Preferred 3 where R₂ is H.

Specifically Preferred for reasons of their highest herbicidal activity,greatest plant growth regulant activity and/or most favorable ease ofsynthesis are:

N-[(4-chloro-6-ethoxypyrimidin-2-yl)aminocarbonyl]-2-(propylsulfonyl)benzenesulfonamide,m.p. 220°-222°;

N-[(4-dimethylamino-6-methoxy-1,3,5-triazin-2-yl)-aminocarbonyl]-2-(methylsulfonyl)benzenesulfonamide,m.p. 192°-195°;

N-[(4-dimethylamino-6-methoxy-1,3,5-triazin-2-yl)-aminocarbonyl]-2-(propylsulfonyl)benzenesulfonamide,m.p. 208°-210°; and

N-[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-2-(propylsulfonyl)benzenesulfonamide,m.p. 193°-195°.

SYNTHESIS

As shown in Equation 1, the compounds of Formula I can be prepared byreacting an appropriate 2-aminopyrimidine or 2-amino-1,3,5-triazine ofFormula III with an appropriately substituted sulfonyl isocyanate ofFormula IIa; R₁ is R₃ SO₂ or R₃ S; R₂, R₃, X, Y and Z are as previouslydefined.

EQUATION 1 ##STR12##

The reaction is best carried out in an inert aprotic organic solventsuch as methylene chloride, tetrahydrofuran or acetonitrile, at ambientpressure and temperature. The mode of addition is not critical; however,it is often convenient to add the sulfonyl isocyanate to a stirredsuspension of amine III. Since such isocyanates are usually liquid,their addition can be easily controlled.

The reaction is generally exothermic. In some cases, the desired productis insoluble in the warm reaction medium and crystallizes from it inpure form. Products soluble in the reaction medium are isolated byevaporation of the solvent, trituration of the solid residue withsolvents such as 1-chlorobutane or ethyl ether and filtration.

The intermediate sulfonyl isocyanates of Formula IIa can be prepared byreacting corresponding sulfonamides with phosgene in the presence ofn-butyl isocyanate at reflux in a solvent such as xylene, according tothe procedure of H. Ulrich and A. A. Y. Sayigh, Newer Methods ofPreparative Organic Chemistry, Vol. VI, p. 223-241, Academic Press, NewYork and London, W. Foerst Ed. In cases where formation of the desiredsulfonyl isocyanate is difficult by the above procedure, thesulfonylurea formed by the reaction of butyl isocyanate with theappropriate sulfonamide is treated with phosgene according to the abovereference.

These intermediates are prepared from the parent sulfonamides of FormulaIIb as shown in Equation 2 by the reaction of the n-butylsulfonylureawith phosgene as described above. In Equation 2, R₁ is R₃ SO₂ or R₃ Sand R₂ and R₃ are as previously defined.

EQUATION 2 ##STR13##

A mixture of the appropriate sulfonylurea, IV and a catalytic amount of1,4-diaza[2.2.2]bicyclooctane (DABCO) in xylene, chlorobenzene or otherinert solvent of sufficiently high boiling point (e.g. 135° C.) isheated to approximately 135° C. Phosgene is added to the mixture untilan excess of phosgene is present as indicated by a drop in the boilingpoint. The mixture is heated further to drive off the excess phosgene,cooled and filtered to remove a small amount of insoluble by-products.The solvent and alkylisocyanate are removed in vacuo leaving a residuewhich is the crude sulfonylisocyanate IIa.

The sulfonylisocyanates of Formula IIa may also be prepared by reactingsulfonamides of Formula IIb with thionyl chloride and then phosgene astaught in EPO Publication No. 35893.

Certain compounds of Formula I are best prepared by heating a mixture ofthe arylsulfonylphenylcarbamate of Formula IIc and an appropriate2-aminopyrimidine or 2-amino-1,3,5-triazine of Formula III in a solventof sufficiently high boiling point, for example dioxane, as shown inEquation 3. The carbamates of Formula IIc are readily prepared from thecorresponding sulfonamides of Formula IIb, where R₁ and R₂ are aspreviously defined, and diphenylcarbamate in the presence of base.

EQUATION 3 ##STR14##

The compounds of Formula I can also be prepared from the sulfonamides ofFormula IIb and the appropriate heterocyclic carbamate of Formula IIIaas shown in Equation 4. Contacting IIb with trimethylaluminum isfollowed by addition of IIIa. Heating the resulting mixture indichloromethane will give I after acidic workup. The heterocycliccarbamates of Formula IIIa can be readily prepared from thecorresponding amines III by standard literature procedures.

EQUATION 4 ##STR15##

The sulfonamides of Formula IIb can be prepared by a variety ofprocedures reported in the literature. As shown in Equation 5, thethioether of Formula VI may be prepared from the appropriate2-aminothiophenol V and an alkyl halide as described in the literature,e.g., R. N. Prasad et al., Can. J. Chem., 44, 1247 (1966). The formationof the benzenesulfonyl chloride and the corresponding sulfonamide IIdhas been previously described (co-pending application Ser. No. 192,034,filed Sept. 29, 1980). The oxidation of IId to the corresponding2-alkylsulfinyl- or 2-alkylsulfonylbenzenesulfonamides of Formulae IIeand IIf may be carried out utilizing a variety of standard literatureprocedures, including m-chloroperbenzoic acid (C. R. Johnson, et al.,Tetradedron 25, 5649 (1969)), or with aqueous hydrogen peroxide inacetic acid (F. G. Bordwell, et al., J. Amer. Chem. Soc., 77, 1141(1955)).

EQUATION 5 ##STR16##

Compounds of Formula IIb wherein n≠1 may also be prepared from2-halonitrobenzenes of Formula VII where A is a halogen as outlined inEquation 6. Halide displacement in VII by thiols (n=0) or sulfinates(n=2) is widely reported in the literature (for general reviews see,"Organic Chemistry of Sulfur", S. Oae, ed., Plenum Press, New York,1977, pp. 232-233; Reid, "Organic Chemistry of Bivalent Sulfur,"Chemical Publishing Co., New York, Vol. 2, pp. 16-21, 24-29; Vol. 3, pp.11-14; Peach, in Patai, "The Chemistry of the Thiol Group," pt. 2, pp.735-744, John Wiley and Sons, Inc., New York, 1974).

EQUATION 6 ##STR17##

Compounds of Formula IX (n=0 or 2) may also be prepared as shown inEquation 7 (in addition to references cited above, see Zn Obshch. Khim,35 (8) 1361 (1965) and J. Chem. Soc., 763 (1946)). Reduction of IX tothe amine X can be carried out by a variety of standard literatureprocedures, including catalytic hydrogenation (Rylander, "CatalyticHydrogenation over Platinum Metals," pp. 168-202, Academic Press, Inc.,New York, 1967) and reduction with iron (D. Cowsley et al., Synthesis118 (1977)) or stannous chloride (Org. Synth., Coll. Vol. 2, 130 (1943);ibid, 3, 240, 453 (1955)) in acidic medium. Conversion of X to IIb hasbeen discussed previously (Equation 5).

EQUATION 7 ##STR18##

In some cases it is best to oxidize the thioethers of Formula IXa to thecorresponding sulfones IXb prior to reduction and subsequentdiazotization, as shown in Equation 8.

EQUATION 8 ##STR19##

Ortho-lithiation of appropriately substituted benzene derivatives alsoprovides a route to sulfonamides of Formula IIb. As shown in Equation 9,the t-butylbenzenesulfonamides of Formula XI may be ortholithiated [forgeneral review, see H. W. Gschwend et al., Organic Reactions, 26, 1(1979)] and then trapped with sulfur, followed by alkyl halide, ortrapped with a disulfide to give sulfonamides of Formula IId [S.Gronowitz et al., Acta. Chem. Scand., 21, 812 (1967) and Chem. Ber., 99,3215 (1966)]. Reactions of XII with sulfur dioxide, followed by alkylhalide (R₃ -hal.) will give sulfonamides of Formula IIf [JACS, 74, 5177(1952)].

EQUATION 9 ##STR20##

The lithium sulfonates of Formula XIII can also be ortho-lithiated togive compounds of Formula XIV as shown in Equation 10. Treatment of XIVwith sulfur electrophiles as in Equation 9 will give the sulfonates ofFormula XV (for example, see J. C. Martin et al., JOC, 45, 3728 (1980)].Conversion of XV to the sulfonamides of Formula IIb can be accomplishedusing thionyl chloride and a catalytic amount of dimethylformamide andthen treating the sulfonyl chloride with ammonia.

EQUATION 10 ##STR21##

Sulfonamides of Formula IId can also be prepared by reaction of thechlorosulfonamides of Formula IIg and the appropriate mercaptan ofFormula XVI in a high boiling solvent, for example, dimethylformamide,as shown in Equation 11. The preparation of the sulfonamides IIg isdescribed in U.S. Pat. No. 4,169,719 and U.S. Pat. No. 4,127,405, whichare herein incorporated by reference.

EQUATION 11 ##STR22##

Compounds of Formula I may also be prepared by the reaction of thesubstituted sulfonamides of Formula IIb with an appropriate heterocyclicisocyanate as previously described (co-pending applications Ser. No.098,725 and Ser. No. 098,722).

Compounds of Formula Ib, where R₁ is equal to SOR₃ can be prepared fromthe appropriate compounds of Formula Ia where R₁ is equal to SR₃ ; R₂,X, Y and Z being as previously defined, by oxidation withm-chloroperbenzoic acid according to Equation 12.

EQUATION 12 ##STR23##

The reaction can be carried out by mixing equivalent amounts of Ia withm-chloroperbenzoic acid in an inert solvent such as chloroform andstirring at 0° C. to reflux for 12-24 hours after which the insolublem-chlorobenzoic acid produced is removed by filtration and thechloroform solution containing the desired sulfoxide is concentrated toyield the crude product. The product can be purified further bydissolving it in aqueous base of pH 10 and adjusting the pH to 4 toprecipitate the desired compound while leaving the m-chlorobenzoic acidin solution as its sodium salt. Treatment of Ia with one equivalent ofhydrogen peroxide in glacial acetic acid at 0° C. to room temperaturewill also give sulfoxide Ib.

The synthesis of heterocyclic amine derivatives has been reviewed in"The Chemistry of Heterocyclic Compounds," a series published byInterscience Publ., New York and London. 2-Aminopyrimidines aredescribed by D. J. Brown in "The Pyrimidines", Vol. XVI of the aboveseries. 2-Amino-1,3,5-triazines can be synthesized according to themethods described by E. M. Smolin and L. Rapaport in "s-Triazines andDerivatives," Vol. XIII of the same series.

Agriculturally suitable salts of compounds of Formula I are also usefulherbicides and can be prepared in a number of ways known to the art. Forexample, metal salts can be made by contacting compounds of Formula Iwith a solution of an alkali or alkaline earth metal salt having asufficiently basic anion (e.g., hydroxide, alkoxide, carbonate orhydroxide). Quaternary amine salts can be made by similar techniques.

Salts of compounds of Formula I can also be prepared by exchange of onecation for another. Cationic exchange can be effected by direct contactof an aqueous solution of a salt of a compound of Formula I (e.g.,alkali or quaternary amine salt) with a solution containing the cationto be exchanged. This method is most effective when the desired saltcontaining the exchanged cation is insoluble in water and can beseparated by filtration.

Exchange may also be effected by passing an aqueous solution of a saltof a compound of Formula I (e.g., an alkali metal or quaternary aminesalt) through a column packed with a cation exchange resin containingthe cation to be exchanged for that of the original salt and the desiredproduct is eluted from the column. This method is particularly usefulwhen the desired salt is water-soluble.

Acid addition salts, useful in this invention, can be obtained byreacting a compound of Formula I with a suitable acid, e.g.,p-toluenesulfonic acid, trichloroacetic acid or the like.

The compounds of this invention and their preparation are furtherillustrated by the following examples wherein temperatures are given indegrees centigrade and parts are by weight unless otherwise designated.

EXAMPLE 1N-[(4-Chloro-6-ethoxypyrimidin-2-yl)aminocarbonyl]-2-(propylsulfonyl)benzenesulfonamide

To a suspension of 2-propylsulfonylbenzenesulfonyl isocyanate (1.67 g,5.76 mmol) in dry acetonitrile was added2-amino-4-chloro-6-ethoxypyrimidine (1.00 g, 5.76 mmol). After stirringat room temperature overnight, the reaction mixture was filtered and thesolid washed with 1-chlorobutane to give the product as a white powdermelting at 220°-222° C.

EXAMPLE 2N-[(4-Chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-2-(propylsulfonyl)benzenesulfonamide

To a suspension of 2-propylsulfonylbenzenesulfonyl isocyanate (1.74 g,6.00 mmol) in dry acetonitrile (25 ml) was added2-amino-4-chloro-6-ethoxypyrimidine (1.00 g, 6.00 mmol). After stirringat room temperature overnight, the reaction mixture was filtered toyield the product as a white powder melting at 193°-195° C.

EXAMPLE 3N-[(4-Dimethylamino-6-methoxy-1,3,5-triazin-2-yl)-aminocarbonyl]-2-(methylsulfonyl)benzenesulfonamide

To a suspension of 2-amino-4-dimethylamino-6-methoxy-1,3,5-triazine(1.02 g, 6.00 mmol) in dry acetonitrile (30 ml) was added2-methylsulfonylbenzenesulfonyl isocyanate (1.50 g, 6.00 mmol). Afterstirring at room temperature overnight, the reaction mixture wasfiltered and the solid washed with acetonitrile to give the product as awhite powder with a melting point of 192°-195° C.

Using procedures similar to those given in Examples 1-3 and Equations1-12, the following compounds may be prepared.

                  TABLE I                                                         ______________________________________                                         ##STR24##                                                                    R.sub.1                R.sub.2 m.p. (°C.)                              ______________________________________                                        SCH.sub.3              H                                                      SOCH.sub.3             H                                                      SO.sub.2 CH.sub.3      H       231-235°                                SC.sub.2 H.sub.5       H                                                      SOC.sub.2 H.sub.5      H                                                      SO.sub.2 C.sub.2 H.sub.5                                                                             H       151-155°                                S(CH.sub.2).sub.2 CH.sub.3                                                                           H                                                      SO(CH.sub.2).sub.2 CH.sub.3                                                                          H                                                      SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                                   H                                                      SCH(CH.sub.3).sub.2    H                                                      SOCH(CH.sub.3).sub.2   H                                                      SO.sub.2 CH(CH.sub.3).sub.2                                                                          H                                                      S(CH.sub.2).sub.3 CH.sub.3                                                                           H                                                      SO(CH.sub.2).sub.3 CH.sub.3                                                                          H                                                      SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                                   H                                                      SCH.sub.2 CH(CH.sub.3).sub.2                                                                         H                                                      SOCH.sub.2 CH(CH.sub.3).sub.2                                                                        H                                                      SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                                 H                                                      SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                                       H                                                      SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                                      H                                                      SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                               H                                                      SC(CH.sub.3).sub.3     H                                                      SOC(CH.sub.3).sub.3    H                                                      SO.sub.2 C(CH.sub.3).sub.3                                                                           H                                                      SCH.sub.2 CHCH.sub.2   H                                                      SOCH.sub.2 CHCH.sub.2  H                                                      SO.sub.2 CH.sub.2 CHCH.sub.2                                                                         H                                                      SCHCHCH.sub.3          H                                                      SOCHCHCH.sub.3         H                                                      SO.sub.2 CHCHCH.sub.3  H                                                      SCH.sub.2 CHCHCH.sub.3 H                                                      SOCH.sub.2 CHCHCH.sub.3                                                                              H                                                      SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                                       H                                                      SCH.sub.2 C(CH.sub.3)CH.sub.2                                                                        H                                                      SOCH.sub.2 C(CH.sub.3)CH.sub.2                                                                       H                                                      SO.sub.2 CH.sub.2 C(CH.sub.3)CH.sub.2                                                                H                                                       ##STR25##             H                                                       ##STR26##             H                                                       ##STR27##             H                                                      SO.sub.2 CH.sub.3      3-Cl                                                   SO.sub.2 CH.sub.3      3-CH.sub.3                                             SO.sub.2 CH.sub.3      3-CF.sub.3                                             SO.sub.2 CH.sub.3      5-F                                                    SO.sub.2 CH.sub.3      5-Cl                                                   SO.sub.2 CH.sub.3      5-Br                                                   SO.sub.2 CH.sub.3      5-CH.sub.3                                             SO.sub.2 CH.sub.3      5-OCH.sub.3                                            SO.sub.2 CH.sub.3      5-CF.sub.3                                             SO.sub.2 CH.sub.3      5-NO.sub.2                                             SO.sub.2 CH.sub.3      6-Cl                                                   SO.sub.2 CH.sub.3      6-CH.sub.3                                             SO.sub.2 CH.sub.3      6-OCH.sub.3                                            SO.sub.2 C.sub.2 H.sub.5                                                                             3-CH.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                             3-Cl                                                   SO.sub.2 C.sub.2 H.sub.5                                                                             3-CF.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                             3-Cl                                                   SO.sub.2 C.sub.2 H.sub.5                                                                             5-Br                                                   SO.sub.2 C.sub.2 H.sub.5                                                                             5-CH.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                             5-CF.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                             5-OCH.sub.3                                            SO.sub.2 C.sub.2 H.sub.5                                                                             6-CH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                                   3-Br                                                   SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                                   3-CH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                                   5-Cl                                                   SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                                   5-CH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                                   5-Br                                                   SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                                   5-CF.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                                   5-OCH.sub.3                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                                   6-CH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                                   6-Cl                                                   SO.sub.2 CH(CH.sub.3).sub.2                                                                          5-CF.sub.3                                             S(CH.sub.2).sub.3 CH.sub.3                                                                           3-CH.sub.3                                             SOCH.sub.2 CH(CH.sub.3).sub.2                                                                        5-CH.sub.3                                             SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                               5-Br                                                   SO.sub.2 C(CH.sub.3).sub.3                                                                           5-CF.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                         3-CH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                         5-CF.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                         5-Br                                                   SO.sub.2 CH.sub.2 CHCH.sub.2                                                                         5-CH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                         6-NO.sub.2                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                         6-OCH.sub.3                                            SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                                       5-CF.sub.3                                              ##STR28##             3-CH.sub.3                                              ##STR29##             5-Br                                                    ##STR30##             5-NO.sub.2                                              ##STR31##             6-F                                                    ______________________________________                                    

                  TABLE II                                                        ______________________________________                                         ##STR32##                                                                    R.sub.1      R.sub.2   X        Y    m.p. (°C.)                        ______________________________________                                        S(CH.sub.2).sub.2 CH.sub.3                                                                 H         CH.sub.3 Cl                                            SO(CH.sub.2).sub.2 CH.sub.3                                                                H         CH.sub.3 Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         H         CH.sub.3 Cl                                            SCH(CH.sub.3).sub.2                                                                        H         CH.sub.3 Cl                                            SOCH(CH.sub.3).sub.2                                                                       H         CH.sub.3 Cl                                            SO.sub.2 CH(CH.sub.3).sub.2                                                                H         CH.sub.3 Cl                                            S(CH.sub.2).sub.3 CH.sub.3                                                                 H         CH.sub.3 Cl                                            SO(CH.sub.2).sub.3 CH.sub.3                                                                H         CH.sub.3 Cl                                            SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                         H         CH.sub.3 Cl                                            SCH.sub.2 CH(CH.sub.3).sub.2                                                               H         CH.sub.3 Cl                                            SOCH.sub.2 CH(CH.sub.3).sub.2                                                              H         CH.sub.3 Cl                                            SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                       H         CH.sub.3 Cl                                            SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         CH.sub.3 Cl                                            SOCH(CH.sub.3 (CH.sub.2 CH.sub.3                                                           H         CH.sub.3 Cl                                            SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                     H         CH.sub.3 Cl                                            SC(CH.sub.3).sub.3                                                                         H         CH.sub.3 Cl                                            SOC(CH.sub.3).sub.3                                                                        H         CH.sub.3 Cl                                            SO.sub.2 C(CH.sub.3).sub.3                                                                 H         CH.sub.3 Cl                                             ##STR33##   H         CH.sub.3 Cl                                             ##STR34##   H         CH.sub.3 Cl                                             ##STR35##   H         CH.sub.3 Cl                                            S(CH.sub.2).sub.2 CH.sub.3                                                                 H         OCH.sub.3                                                                              Cl   160-162°                          SO(CH.sub.2).sub.2 CH.sub.3                                                                H         OCH.sub.3                                                                              Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         H         OCH.sub.3                                                                              Cl   193-195°                          SCH(CH.sub.3).sub.2                                                                        H         OCH.sub.3                                                                              Cl                                            SOCH(CH.sub.3).sub.2                                                                       H         OCH.sub.3                                                                              Cl                                            SO.sub.2 CH(CH.sub.3).sub.2                                                                H         OCH.sub.3                                                                              Cl                                            S(CH.sub.2).sub.3 CH.sub.3                                                                 H         OCH.sub.3                                                                              Cl                                            SO(CH.sub.2).sub.3 CH.sub.3                                                                H         OCH.sub.3                                                                              Cl                                            SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                         H         OCH.sub.3                                                                              Cl                                            SCH.sub.2 CH(CH.sub.3).sub.2                                                               H         OCH.sub.3                                                                              Cl                                            SOCH.sub.2 CH(CH.sub.3).sub.2                                                              H         OCH.sub.3                                                                              Cl                                            SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                       H         OCH.sub.3                                                                              Cl                                            SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         OCH.sub.3                                                                              Cl                                            SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                            H         OCH.sub.3                                                                              Cl                                            SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                     H         OCH.sub.3                                                                              Cl                                            SC(CH.sub.3).sub.3                                                                         H         OCH.sub.3                                                                              Cl                                            SOC(CH.sub.3).sub.3                                                                        H         OCH.sub.3                                                                              Cl                                            SO.sub.2 C(CH.sub.3).sub.3                                                                 H         OCH.sub.3                                                                              Cl                                             ##STR36##   H         OCH.sub.3                                                                              Cl                                             ##STR37##   H         OCH.sub.3                                                                              Cl                                             ##STR38##   H         OCH.sub.3                                                                              Cl                                            S(CH.sub.2).sub.2 CH.sub.3                                                                 H         OC.sub.2 H.sub.5                                                                       Cl                                            SO(CH.sub.2).sub.2 CH.sub.3                                                                H         OC.sub.2 H.sub.5                                                                       Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         H         OC.sub.2 H.sub.5                                                                       Cl   220-222°                          SCH(CH.sub.3).sub.2                                                                        H         OC.sub.2 H.sub.5                                                                       Cl                                            SOCH(CH.sub.3).sub.2                                                                       H         OC.sub.2 H.sub.5                                                                       Cl                                            SO.sub.2 CH(CH.sub.3).sub.2                                                                H         OC.sub.2 H.sub.5                                                                       Cl                                            S(CH.sub.2).sub.3 CH.sub.3                                                                 H         OC.sub.2 H.sub.5                                                                       Cl                                            SO(CH.sub.2).sub.3 CH.sub.3                                                                H         OC.sub.2 H.sub.5                                                                       Cl                                            SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                         H         OC.sub.2 H.sub.5                                                                       Cl                                            SCH.sub.2 CH(CH.sub.3).sub.2                                                               H         OC.sub.2 H.sub.5                                                                       Cl                                            SOCH.sub.2 CH(CH.sub.3).sub.2                                                              H         OC.sub.2 H.sub.5                                                                       Cl                                            SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                       H         OC.sub.2 H.sub.5                                                                       Cl                                            SCH(CH.sub.3 CH.sub.2 CH.sub.3                                                             H         OC.sub.2 H.sub.5                                                                       Cl                                            SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                            H         OC.sub.2 H.sub.5                                                                       Cl                                            SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                     H         OC.sub.2 H.sub.5                                                                       Cl                                            SC(CH.sub.3).sub.3                                                                         H         OC.sub.2 H.sub.5                                                                       Cl                                            SOC(CH.sub. 3).sub.3                                                                       H         OC.sub.2 H.sub.5                                                                       Cl                                            SO.sub.2 C(CH.sub.3).sub.3                                                                 H         OC.sub.2 H.sub.5                                                                       Cl                                             ##STR39##   H         OC.sub.2 H.sub.5                                                                       Cl                                             ##STR40##   H         OC.sub.2 H.sub.5                                                                       Cl                                             ##STR41##   H         OC.sub.2 H.sub.5                                                                       Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         H         CH.sub.3 F                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         H         CH.sub.3 Br                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         3-Cl      CH.sub.3 Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         3-OCH.sub.3                                                                             CH.sub.3 Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         3-CF.sub.3                                                                              CH.sub.3 Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         5-F       CH.sub.3 Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         5-Cl      CH.sub.3 Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         5-Br      CH.sub.3 Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         5-CH.sub.3                                                                              CH.sub.3 Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         5-OCH.sub.3                                                                             CH.sub.3 Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         5-CF.sub.3                                                                              CH.sub.3 Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         5-NO.sub.2                                                                              CH.sub.3 Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         6-Cl      CH.sub.3 Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         6-CH.sub.3                                                                              CH.sub.3 Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         6-OCH.sub.3                                                                             CH.sub.3 Cl                                            SO.sub.2 CH(CH.sub.3).sub.2                                                                5-CH.sub.3                                                                              CH.sub.3 Cl                                            SO.sub.2 CH(CH.sub.3).sub.2                                                                5-CF.sub.3                                                                              CH.sub.3 Cl                                            SO.sub.2 CH(CH.sub.3).sub.2                                                                5-Cl      CH.sub.3 Cl                                            SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                         3-CH.sub.3                                                                              CH.sub.3 Cl                                            SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                         5-Cl      CH.sub.3 Cl                                            SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                         5-OCH.sub.3                                                                             CH.sub.3 Cl                                            SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         CH.sub.3 F                                             SOCH.sub.2 CH(CH.sub.3).sub.2                                                              H         CH.sub.3 Br                                            SO.sub.2 C(CH.sub.3).sub.3                                                                 5-Br      CH.sub.3 Cl                                             ##STR42##   H         CH.sub.3 F                                              ##STR43##   H         CH.sub.3 Br                                             ##STR44##   6-Br      CH.sub.3 Cl                                             ##STR45##   5-CF.sub.3                                                                              CH.sub.3 Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         H         OCH.sub.3                                                                              F                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         H         OCH.sub.3                                                                              Br                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         5-CH.sub.3                                                                              OCH.sub.3                                                                              Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         5-Br      OCH.sub.3                                                                              Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         5-OCH.sub.3                                                                             OCH.sub.3                                                                              Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         5-CF.sub.3                                                                              OCH.sub.3                                                                              Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         6-CH.sub.3                                                                              OCH.sub.3                                                                              Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         6-Cl OCH.sub.3                                                                          Cl                                                     SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                         3-F       OCH.sub.3                                                                              Cl                                            SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                         3-NO.sub.2                                                                              OCH.sub.3                                                                              Cl                                            SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                         5-CH.sub.3                                                                              OCH.sub.3                                                                              Cl                                            SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                         5-OCF.sub.3                                                                             OCH.sub.3                                                                              Cl                                            SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                     H         OCH.sub.3                                                                              F                                             SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                     H         OCH.sub.3                                                                              Br                                            SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                     5-Cl      OCH.sub.3                                                                              Cl                                            SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                     5-OCH.sub.3                                                                             OCH.sub.3                                                                              Cl                                            SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                     5-CF.sub.3                                                                              OCH.sub.3                                                                              Cl                                            SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                     5-NO.sub.2                                                                              OCH.sub.3                                                                              Cl                                             ##STR46##   H         OCH.sub.3                                                                              F                                              ##STR47##   H         OCH.sub.3                                                                              Br                                             ##STR48##   6-Cl      OCH.sub.3                                                                              Cl                                            S(CH.sub.2).sub.2 CH.sub.3                                                                 H         OCH.sub.3                                                                              F                                             S(CH.sub.2).sub.2 CH.sub.3                                                                 H         OCH.sub.3                                                                              Br                                            S(CH.sub.2).sub.2 CH.sub.3                                                                 5-CF.sub.3                                                                              OCH.sub.3                                                                              Cl                                            S(CH.sub.2).sub.2 CH.sub.3                                                                 6-Cl      OCH.sub.3                                                                              Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         H         OC.sub.2 H.sub.5                                                                       F                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         H         OC.sub.2 H.sub.5                                                                       Br                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         3-CF.sub.3                                                                              OC.sub.2 H.sub.5                                                                       Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         5-Cl      OC.sub.2 H.sub.5                                                                       Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         4-OCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                       Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         5-NO.sub.2                                                                              OC.sub.2 H.sub.5                                                                       Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         5-CH.sub.3                                                                              OC.sub.2 H.sub.5                                                                       Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         6-CH.sub.3                                                                              OC.sub.2 H.sub.5                                                                       Cl                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                         6-Cl      OC.sub.2 H.sub.5                                                                       Cl                                            SOCH(CH.sub.3).sub.2                                                                       3-CH.sub.3                                                                              OC.sub.2 H.sub.5                                                                       Cl                                            SOCH(CH.sub.3).sub.2                                                                       5-Cl      OC.sub.2 H.sub.5                                                                       Cl                                            SOCH(CH.sub.3).sub.2                                                                       6-Br      OC.sub.2 H.sub.5                                                                       Cl                                            SCH.sub.2 CH(CH.sub.3).sub.2                                                               3-CF.sub.3                                                                              OC.sub.2 H.sub.5                                                                       Cl                                            SCH.sub.2 CH(CH.sub. 3).sub.2                                                              5-OCH.sub.3                                                                             OC.sub.2 H.sub.5                                                                       Cl                                            SCH.sub.2 CH(CH.sub.3).sub.2                                                               6-NO.sub.2                                                                              OC.sub.2 H.sub.5                                                                       Cl                                            SO.sub.2 C(CH.sub.3).sub.3                                                                 H         OC.sub.2 H.sub.5                                                                       F                                             SO.sub.2 C(CH.sub.3).sub.3                                                                 H         OC.sub.2 H.sub.5                                                                       Br                                            SO.sub.2 C(CH.sub.3).sub.3                                                                 5-Br      OC.sub.2 H.sub.5                                                                       Cl                                            SO.sub.2 C(CH.sub.3).sub.3                                                                 5-CH.sub.3                                                                              OC.sub.2 H.sub.5                                                                       Cl                                            SO.sub.2 C(CH.sub.3).sub.3                                                                 6-CF.sub.3                                                                              OC.sub.2 H.sub.5                                                                       Cl                                             ##STR49##   3-Br      OC.sub.2 H.sub.5                                                                       Cl                                             ##STR50##   5-CF.sub.3                                                                              OC.sub.2 H.sub.5                                                                       Cl                                             ##STR51##   6-CH.sub.3                                                                              OC.sub.2 H.sub.5                                                                       Cl                                            SO.sub.2 CH.sub.3                                                                          H         OC.sub.2 H.sub.5                                                                       Cl   188-190°                          ______________________________________                                    

                  TABLE III                                                       ______________________________________                                         ##STR52##                                                                    R.sub.1       R.sub.2   X          m.p. (°C.)                          ______________________________________                                        SCH.sub.3     H         CH.sub.3                                              SOCH.sub.3    H         CH.sub.3                                              SO.sub.2 CH.sub.3                                                                           H         CH.sub.3   239-242°                            SC.sub.2 H.sub.5                                                                            H         CH.sub.3                                              SOC.sub.2 H.sub.5                                                                           H         CH.sub.3                                              SO.sub.2 C.sub.2 H.sub.5                                                                    H         CH.sub.3                                              S(CH.sub.2).sub.2 CH.sub.3                                                                  H         CH.sub.3                                              SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         CH.sub.3                                              SCH(CH.sub.3).sub.2                                                                         H         CH.sub.3                                              SOCH(CH.sub.3).sub.2                                                                        H         CH.sub.3                                              SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         CH.sub.3                                              S(CH.sub.2).sub.3 CH.sub.3                                                                  H         CH.sub.3                                              SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         CH.sub.3                                              SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         CH.sub.3                                              SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         CH.sub.3                                              SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         CH.sub.3                                              SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         CH.sub.3                                              SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         CH.sub.3                                              SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         CH.sub.3                                              SC(CH.sub.3).sub.3                                                                          H         CH.sub.3                                              SOC(CH.sub.3).sub.3                                                                         H         CH.sub.3                                              SO.sub.2 C(CH.sub.3).sub.3                                                                  H         CH.sub.3                                              SCH.sub.2 CHCH.sub.2                                                                        H         CH.sub.3                                              SOCH.sub.2 CHCH.sub.2                                                                       H         CH.sub.3                                              SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         CH.sub.3                                              SCH.sub.2 CHCHCH.sub.3                                                                      H         CH.sub.3                                              SOCH.sub.2 CHCHCH.sub.3                                                                     H         CH.sub.3                                              SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         CH.sub.3                                               ##STR53##    H         CH.sub.3                                               ##STR54##    H         CH.sub.3                                               ##STR55##                                                                    SCH.sub. 3    H         OCH.sub.3                                             SOCH.sub.3    H         OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                           H         OCH.sub.3  208-210°                            SC.sub.2 H.sub.5                                                                            H         OCH.sub.3                                             SOC.sub.2 H.sub.5                                                                           H         OCH.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                    H         OCH.sub.3  189-190°                            S(CH.sub.2).sub.2 CH.sub.3                                                                  H         OCH.sub.3                                             SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         OCH.sub.3                                             SCH(CH.sub.3).sub.2                                                                         H         OCH.sub.3                                             SOCH(CH.sub.3).sub.2                                                                        H         OCH.sub.3                                             SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         OCH.sub.3                                             S(CH.sub.2).sub.3 CH.sub.3                                                                  H         OCH.sub.3                                             SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         OCH.sub.3                                             SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         OCH.sub.3                                             SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         OCH.sub.3                                             SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         OCH.sub.3                                             SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         OCH.sub.3                                             SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         OCH.sub.3                                             SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         OCH.sub.3                                             SC(CH.sub.3).sub.3                                                                          H         OCH.sub.3                                             SOC(CH.sub.3).sub.3                                                                         H         OCH.sub.3                                             SO.sub.2 C(CH.sub.3).sub. 3                                                                 H         OCH.sub.3                                             SCH.sub.2 CHCH.sub.2                                                                        H         OCH.sub.3                                             SOCH.sub.2 CHCH.sub.2                                                                       H         OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         OCH.sub.3                                             SCH.sub.2 CHCHCH.sub.3                                                                      H         OCH.sub.3                                             SOCH.sub.2 CHCHCH.sub.3                                                                     H         OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         OCH.sub.3                                              ##STR56##    H         OCH.sub.3                                              ##STR57##    H         OCH.sub.3                                              ##STR58##    H         OCH.sub.3                                             SCH.sub.3     H         C.sub.2 H.sub.5                                       SOCH.sub.3    H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.3                                                                           H         C.sub.2 H.sub.5                                       SC.sub.2 H.sub.5                                                                            H         C.sub.2 H.sub.5                                       SOC.sub.2 H.sub.5                                                                           H         C.sub.2 H.sub.5                                       SO.sub.2 C.sub.2 H.sub.5                                                                    H         C.sub.2 H.sub.5                                       S(CH.sub.2).sub.2 CH.sub.3                                                                  H         C.sub.2 H.sub.5                                       SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         C.sub.2 H.sub.5                                       SO.sub.2 (CH.sub.2 ).sub.2 CH.sub.3                                                         H         C.sub.2 H.sub.5                                       SCH(CH.sub.3).sub.2                                                                         H         C.sub.2 H.sub.5                                       SOCH(CH.sub.3).sub.2                                                                        H         C.sub.2 H.sub.5                                       SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         C.sub.2 H.sub.5                                       S(CH.sub.2).sub.3 CH.sub.3                                                                  H         C.sub.2 H.sub.5                                       SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         C.sub.2 H.sub.5                                       SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         C.sub.2 H.sub.5                                       SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         C.sub.2 H.sub.5                                       SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         C.sub.2 H.sub.5                                       SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         C.sub.2 H.sub.5                                       SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         C.sub.2 H.sub.5                                       SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         C.sub.2 H.sub.5                                       SC(CH.sub.3).sub.3                                                                          H         C.sub.2 H.sub.5                                       SOC(CH.sub.3).sub.3                                                                         H         C.sub.2 H.sub.5                                       SO.sub.2 C(CH.sub.3).sub.3                                                                  H         C.sub.2 H.sub.5                                       SCH.sub.2 CHCH.sub.2                                                                        H         C.sub.2 H.sub.5                                       SOCH.sub.2 CHCH.sub.2                                                                       H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         C.sub.2 H.sub.5                                       SCH.sub.2 CHCHCH.sub.3                                                                      H         C.sub.2 H.sub.5                                       SOCH.sub.2 CHCHCH.sub.3                                                                     H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         C.sub.2 H.sub.5                                        ##STR59##    H         C.sub.2 H.sub.5                                        ##STR60##    H         C.sub.2 H.sub.5                                        ##STR61##    H         C.sub.2 H.sub.5                                       SCH.sub.3     H         OC.sub.2 H.sub.5                                      SOCH.sub.3    H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.3                                                                           H         OC.sub.2 H.sub.5                                      SC.sub.2 H.sub.5                                                                            H         OC.sub.2 H.sub.5                                      SOC.sub.2 H.sub.5                                                                           H         OC.sub.2 H.sub.5                                      SO.sub.2 C.sub.2 H.sub.5                                                                    H         OC.sub.2 H.sub.5                                      S(CH.sub.2).sub.2 CH.sub.3                                                                  H         OC.sub.2 H.sub.5                                      SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         OC.sub.2 H.sub.5                                      SCH(CH.sub.3).sub.2                                                                         H         OC.sub.2 H.sub.5                                      SOCH(CH.sub.3).sub.2                                                                        H         OC.sub.2 H.sub.5                                      SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         OC.sub.2 H.sub.5                                      S(CH.sub.2).sub.3 CH.sub.3                                                                  H         OC.sub.2 H.sub.5                                      SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         OC.sub.2 H.sub.5                                      SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         OC.sub.2 H.sub.5                                      SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         OC.sub.2 H.sub.5                                      SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         OC.sub.2 H.sub.5                                      SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         OC.sub.2 H.sub.5                                      SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         OC.sub.2 H.sub.5                                      SC(CH.sub.3).sub.3                                                                          H         OC.sub.2 H.sub.5                                      SOC(CH.sub.3).sub.3                                                                         H         OC.sub.2 H.sub.5                                      SO.sub.2 C(CH.sub.3).sub.3                                                                  H         OC.sub.2 H.sub.5                                      SCH.sub.2 CHCH.sub.2                                                                        H         OC.sub.2 H.sub.5                                      SOCH.sub.2 CHCH.sub.2                                                                       H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         OC.sub.2 H.sub.5                                      SCH.sub.2 CHCHCH.sub.3                                                                      H         OC.sub.2 H.sub.5                                      SOCH.sub.2 CHCHCH.sub.3                                                                     H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         OC.sub.2 H.sub.5                                       ##STR62##    H         OC.sub.2 H.sub.5                                       ##STR63##    H         OC.sub.2 H.sub.5                                       ##STR64##    H         OC.sub.2 H.sub.5                                      SCH.sub.3     H         CH.sub.2 OCH.sub.3                                    SOCH.sub.3    H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.3                                                                           H         CH.sub.2 OCH.sub.3                                    SC.sub.2 H.sub.5                                                                            H         CH.sub.2 OCH.sub.3                                    SOC.sub.2 H.sub.5                                                                           H         CH.sub.2 OCH.sub.3                                    SO.sub.2 C.sub.2 H.sub.5                                                                    H         CH.sub.2 OCH.sub.3                                    S(CH.sub.2).sub.2 CH.sub.3                                                                  H         CH.sub.2 OCH.sub.3                                    SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         CH.sub.2 OCH.sub.3                                    SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         CH.sub.2 OCH.sub.3                                    SCH(CH.sub.3).sub.2                                                                         H         CH.sub.2 OCH.sub.3                                    SOCH(CH.sub.3).sub.2                                                                        H         CH.sub.2 OCH.sub.3                                    SO.sub. 2 CH(CH.sub.3).sub.2                                                                H         CH.sub.2 OCH.sub.3                                    S(CH.sub.2).sub.3 CH.sub.3                                                                  H         CH.sub.2 OCH.sub.3                                    SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         CH.sub.2 OCH.sub.3                                    SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         CH.sub.2 OCH.sub.3                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         CH.sub.2 OCH.sub.3                                    SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         CH.sub.2 OCH.sub.3                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         CH.sub.2 OCH.sub.3                                    SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         CH.sub.2 OCH.sub.3                                    SC(CH.sub.3).sub.3                                                                          H         CH.sub.2 OCH.sub.3                                    SOC(CH.sub.3).sub.3                                                                         H         CH.sub.2 OCH.sub.3                                    SO.sub.2 C(CH.sub.3).sub.3                                                                  H         CH.sub.2 OCH.sub.3                                    SCH.sub.2 CHCH.sub.2                                                                        H         CH.sub.2 OCH.sub.3                                    SOCH.sub.2 CHCH.sub.2                                                                       H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         CH.sub.2 OCH.sub.3                                    SCH.sub.2 CHCHCH.sub.3                                                                      H         CH.sub.2 OCH.sub.3                                    SOCH.sub.2 CHCHCH.sub.3                                                                     H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         CH.sub.2 OCH.sub.3                                     ##STR65##    H         CH.sub.2 OCH.sub.3                                     ##STR66##    H         CH.sub.2 OCH.sub.3                                     ##STR67##    H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.3                                                                           3-CH.sub.3                                                                              CH.sub.3                                              SO.sub.2 CH.sub.3                                                                           5-CF.sub.3                                                                              CH.sub.3                                              SO.sub.2 CH.sub.3                                                                           5-Cl      OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                           5-OCH.sub.3                                                                             C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.3                                                                           5-NO.sub.2                                                                              OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.3                                                                           6-CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                    SC.sub.2 H.sub.5                                                                            5-CH.sub.3                                                                              CH.sub.3                                              SOC.sub.2 H.sub.5                                                                           5-CF.sub.3                                                                              OCH.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                    5-Cl      C.sub.2 H.sub.5                                       SO.sub.2 C.sub.2 H.sub.5                                                                    6-Br      OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          3-CH.sub.3                                                                              CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          3-Br      OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-CH.sub.3                                                                              C.sub.2 H.sub.5                                       SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-CF.sub.3                                                                              OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-OCH.sub.3                                                                             CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-Cl      CH.sub.2 OCH.sub.3                                    SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          6-NO.sub.2                                                                              CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          6-CH.sub.3                                                                              C.sub.2 H.sub.5                                       S(CH.sub.2).sub.3 CH.sub.3                                                                  5-CH.sub.3                                                                              OC.sub.2 H.sub.5                                      SO(CH.sub.2).sub.3 CH.sub.3                                                                 5-CF.sub.3                                                                              OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                3-Br      CH.sub.3                                              SO.sub.2 CH.sub.2 CHCH.sub.2                                                                3-Cl      OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                5-CH.sub.3                                                                              OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CHCH.sub.2                                                                5-OCH.sub.3                                                                             C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCH.sub.3                                                                5-CF.sub.3                                                                              C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCH.sub.2                                                                6-NO.sub.2                                                                              CH.sub.2 OCH.sub.3                                    SCH.sub.2 C(CH.sub.3)CH.sub.2                                                               5-CF.sub.3                                                                              OCH.sub.3                                              ##STR68##    3-CH.sub.3                                                                              OC.sub.2 H.sub.5                                       ##STR69##    5-Cl      CH.sub.2 OCH.sub.3                                    ______________________________________                                    

                  TABLE IV                                                        ______________________________________                                         ##STR70##                                                                    R.sub.1       R.sub.2   X          m.p. (°C.)                          ______________________________________                                        SCH.sub.3     H         CH.sub.3                                              SOCH.sub.3    H         CH.sub.3                                              SO.sub.2 CH.sub.3                                                                           H         CH.sub.3   139-141°                            SC.sub.2 H.sub.5                                                                            H         CH.sub.3                                              SOC.sub.2 H.sub.5                                                                           H         CH.sub.3                                              SO.sub.2 C.sub.2 H.sub.5                                                                    H         CH.sub.3                                              S(CH.sub.2).sub.2 CH.sub.3                                                                  H         CH.sub.3                                              SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         CH.sub.3                                              SCH(CH.sub.3).sub.2                                                                         H         CH.sub.3                                              SOCH(CH.sub.3).sub.2                                                                        H         CH.sub.3                                              SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         CH.sub.3                                              S(CH.sub.2).sub.3 CH.sub.3                                                                  H         CH.sub.3                                              SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         CH.sub.3                                              SO.sub. 2 (CH.sub.2).sub.3 CH.sub.3                                                         H         CH.sub.3                                              SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         CH.sub.3                                              SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         CH.sub.3                                              SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         CH.sub.3                                              SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         CH.sub.3                                              SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         CH.sub.3                                              SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         CH.sub.3                                              SC(CH.sub.3).sub.3                                                                          H         CH.sub.3                                              SOC(CH.sub.3).sub.3                                                                         H         CH.sub.3                                              SO.sub.2 C(CH.sub.3).sub.3                                                                  H         CH.sub.3                                              SCH.sub.2 CHCH.sub.2                                                                        H         CH.sub.3                                              SOCH.sub.2 CHCH.sub.2                                                                       H         CH.sub.3                                              SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         CH.sub.3                                              SCH.sub.2 CHCHCH.sub.3                                                                      H         CH.sub.3                                              SOCH.sub.2 CHCHCH.sub.3                                                                     H         CH.sub.3                                              SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         CH.sub.3                                               ##STR71##    H         CH.sub.3                                               ##STR72##    H         CH.sub.3                                               ##STR73##    H         CH.sub.3                                              SCH.sub.3     H         OCH.sub.3                                             SOCH.sub.3    H         OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                           H         OCH.sub.3  192-195°                            SC.sub.2 H.sub.5                                                                            H         OCH.sub.3                                             SOC.sub.2 H.sub.5                                                                           H         OCH.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                    H         OCH.sub.3  189-192°                            S(CH.sub.2).sub.2 CH.sub.3                                                                  H         OCH.sub.3                                             SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         OCH.sub.3  208-210°                            SCH(CH.sub.3).sub.2                                                                         H         OCH.sub.3                                             SOCH(CH.sub.3).sub.2                                                                        H         OCH.sub.3                                             SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         OCH.sub.3                                             S(CH.sub.2).sub.3 CH.sub.3                                                                  H         OCH.sub.3                                             SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         OCH.sub.3                                             SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         OCH.sub.3                                             SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         OCH.sub.3                                             SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         OCH.sub.3                                             SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         OCH.sub.3                                             SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         OCH.sub.3                                             SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         OCH.sub.3                                             SC(CH.sub.3).sub.3                                                                          H         OCH.sub.3                                             SOC(CH.sub.3).sub.3                                                                         H         OCH.sub.3                                             SO.sub.2 C(CH.sub.3).sub.3                                                                  H         OCH.sub.3                                             SCH.sub.2 CHCH.sub.2                                                                        H         OCH.sub.3                                             SOCH.sub.2 CHCH.sub.2                                                                       H         OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         OCH.sub.3                                             SCH.sub.2 CHCHCH.sub.3                                                                      H         OCH.sub.3                                             SOCH.sub.2 CHCHCH.sub.3                                                                     H         OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         OCH.sub.3                                              ##STR74##    H         OCH.sub.3                                              ##STR75##    H         OCH.sub.3                                              ##STR76##    H         OCH.sub.3                                             SCH.sub.3     H         C.sub.2 H.sub.5                                       SOCH.sub.3    H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.3                                                                           H         C.sub.2 H.sub.5                                       SC.sub.2 H.sub.5                                                                            H         C.sub.2 H.sub.5                                       SOC.sub.2 H.sub.5                                                                           H         C.sub.2 H.sub.5                                       SO.sub.2 C.sub.2 H.sub.5                                                                    H         C.sub.2 H.sub.5                                       S(CH.sub.2).sub.2 CH.sub.3                                                                  H         C.sub.2 H.sub.5                                       SO(CH.sub.2).sub. 2 CH.sub.3                                                                H         C.sub.2 H.sub.5                                       SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         C.sub.2 H.sub.5                                       SCH(CH.sub.3).sub.2                                                                         H         C.sub.2 H.sub.5                                       SOCH(CH.sub.3).sub.2                                                                        H         C.sub.2 H.sub.5                                       SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         C.sub.2 H.sub.5                                       S(CH.sub.2).sub.3 CH.sub.3                                                                  H         C.sub.2 H.sub.5                                       SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         C.sub.2 H.sub.5                                       SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         C.sub.2 H.sub.5                                       SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         C.sub.2 H.sub.5                                       SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         C.sub.2 H.sub.5                                       SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         C.sub.2 H.sub.5                                       SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         C.sub.2 H.sub.5                                       SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         C.sub.2 H.sub.5                                       SC(CH.sub.3).sub.3                                                                          H         C.sub.2 H.sub.5                                       SOC(CH.sub.3).sub.3                                                                         H         C.sub.2 H.sub.5                                       SO.sub.2 C(CH.sub.3).sub.3                                                                  H         C.sub.2 H.sub.5                                       SCH.sub.2 CHCH.sub.2                                                                        H         C.sub.2 H.sub.5                                       SOCH.sub.2 CHCH.sub.2                                                                       H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         C.sub.2 H.sub.5                                       SCH.sub.2 CHCHCH.sub.3                                                                      H         C.sub.2 H.sub.5                                       SOCH.sub.2 CHCHCH.sub.3                                                                     H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         C.sub.2 H.sub.5                                        ##STR77##    H         C.sub.2 H.sub.5                                        ##STR78##    H         C.sub.2 H.sub.5                                        ##STR79##    H         C.sub.2 H.sub.5                                       SCH.sub.3     H         OC.sub.2 H.sub.5                                      SOCH.sub.3    H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.3                                                                           H         OC.sub.2 H.sub.5                                      SC.sub.2 H.sub.5                                                                            H         OC.sub.2 H.sub.5                                      SOC.sub.2 H.sub.5                                                                           H         OC.sub.2 H.sub.5                                      SO.sub.2 C.sub.2 H.sub.5                                                                    H         OC.sub.2 H.sub.5                                      S(CH.sub.2).sub.2 CH.sub.3                                                                  H         OC.sub.2 H.sub.5                                      SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         OC.sub.2 H.sub.5                                                                         91-93° (d)                          SCH(CH.sub.3).sub.2                                                                         H         OC.sub.2 H.sub.5                                      SOCH(CH.sub.3).sub.2                                                                        H         OC.sub.2 H.sub.5                                      SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         OC.sub.2 H.sub.5                                      S(CH.sub.2).sub.3 CH.sub.3                                                                  H         OC.sub.2 H.sub.5                                      SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         OC.sub.2 H.sub.5                                      SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         OC.sub.2 H.sub.5                                      SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         OC.sub.2 H.sub.5                                      SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         OC.sub.2 H.sub.5                                      SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         OC.sub.2 H.sub.5                                      SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         OC.sub.2 H.sub.5                                      SC(CH.sub.3).sub.3                                                                          H         OC.sub.2 H.sub.5                                      SOC(CH.sub.3).sub.3                                                                         H         OC.sub.2 H.sub.5                                      SO.sub.2 C(CH.sub.3).sub.3                                                                  H         OC.sub.2 H.sub.5                                      SCH.sub.2 CHCH.sub.2                                                                        H         OC.sub.2 H.sub.5                                      SOCH.sub.2 CHCH.sub.2                                                                       H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CHCH.sub. 2                                                               H         OC.sub.2 H.sub.5                                      SCH.sub.2 CHCHCH.sub.3                                                                      H         OC.sub.2 H.sub.5                                      SOCH.sub.2 CHCHCH.sub.3                                                                     H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         OC.sub.2 H.sub.5                                       ##STR80##    H         OC.sub.2 H.sub.5                                       ##STR81##    H         OC.sub.2 H.sub.5                                       ##STR82##    H         OC.sub.2 H.sub.5                                      SCH.sub.3     H         CH.sub.2 OCH.sub.3                                    SOCH.sub.3    H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.3                                                                           H         CH.sub.2 OCH.sub.3                                    SC.sub.2 H.sub.5                                                                            H         CH.sub.2 OCH.sub.3                                    SOC.sub.2 H.sub.5                                                                           H         CH.sub.2 OCH.sub.3                                    SO.sub.2 C.sub.2 H.sub.5                                                                    H         CH.sub.2 OCH.sub.3                                    S(CH.sub.2).sub.2 CH.sub.3                                                                  H         CH.sub.2 OCH.sub.3                                    SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         CH.sub.2 OCH.sub.3                                    SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         CH.sub.2 OCH.sub.3                                    SCH(CH.sub.3).sub. 2                                                                        H         CH.sub.2 OCH.sub.3                                    SOCH(CH.sub.3).sub.2                                                                        H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         CH.sub.2 OCH.sub.3                                    S(CH.sub.2).sub.3 CH.sub.3                                                                  H         CH.sub.2 OCH.sub.3                                    SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         CH.sub.2 OCH.sub.3                                    SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         CH.sub.2 OCH.sub.3                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         CH.sub.2 OCH.sub.3                                    SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         CH.sub.2 OCH.sub.3                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         CH.sub.2 OCH.sub.3                                    SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         CH.sub.2 OCH.sub.3                                    SC(CH.sub.3).sub.3                                                                          H         CH.sub.2 OCH.sub.3                                    SOC(CH.sub.3).sub.3                                                                         H         CH.sub.2 OCH.sub.3                                    SO.sub.2 C(CH.sub.3).sub.3                                                                  H         CH.sub.2 OCH.sub.3                                    SCH.sub.2 CHCH.sub.2                                                                        H         CH.sub.2 OCH.sub.3                                    SOCH.sub.2 CHCH.sub.2                                                                       H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         CH.sub.2 OCH.sub.3                                    SCH.sub.2 CHCHCH.sub.3                                                                      H         CH.sub.2 OCH.sub.3                                    SOCH.sub.2 CHCHCH.sub.3                                                                     H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         CH.sub.2 OCH.sub.3                                     ##STR83##    H         CH.sub.2 OCH.sub.3                                     ##STR84##    H         CH.sub.2 OCH.sub.3                                     ##STR85##    H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.3                                                                           3-CH.sub.3                                                                              CH.sub.3                                              SO.sub.2 CH.sub.3                                                                           5-CF.sub.3                                                                              CH.sub.3                                              SO.sub.2 CH.sub.3                                                                           5-Cl      OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                           5-OCH.sub.3                                                                             C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.3                                                                           5-NO.sub.2                                                                              OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.3                                                                           6-CH.sub.3                                                                              CH.sub.2 OCH.sub.3                                    SC.sub.2 H.sub.5                                                                            5-CH.sub.3                                                                              CH.sub.3                                              SOC.sub.2 H.sub.5                                                                           5-CF.sub.3                                                                              OCH.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                    5-Cl      C.sub.2 H.sub.5                                       SO.sub.2 C.sub.2 H.sub.5                                                                    6-Br      OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          3-CH.sub.3                                                                              CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          3-Br      OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-CH.sub.3                                                                              C.sub.2 H.sub.5                                       SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-CF.sub.3                                                                              OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-OCH.sub.3                                                                             CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-Cl      CH.sub.2 OCH.sub.3                                    SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          6-NO.sub.2                                                                              CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          6-CH.sub.3                                                                              C.sub.2 H.sub.5                                       S(CH.sub.2).sub.3 CH.sub.3                                                                  5-CH.sub.3                                                                              OC.sub.2 H.sub.5                                      SO(CH.sub.2).sub.3 CH.sub.3                                                                 5-CF.sub.3                                                                              OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                3-Br      CH.sub.3                                              SO.sub.2 CH.sub.2 CHCH.sub.2                                                                3-Cl      OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                5-CH.sub.3                                                                              OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CHCH.sub.2                                                                5-OCH.sub.3                                                                             C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCH.sub.3                                                                5-CF.sub.3                                                                              C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCH.sub.2                                                                6-NO.sub.2                                                                              CH.sub.2 OCH.sub.3                                    SCH.sub.2 C(CH.sub.3)CH.sub.2                                                               5-CF.sub.3                                                                              OCH.sub.3                                              ##STR86##    3-CH.sub.3                                                                              OC.sub.2 H.sub.5                                       ##STR87##    5-Cl      CH.sub.2 OCH.sub.3                                    ______________________________________                                    

                  TABLE V                                                         ______________________________________                                         ##STR88##                                                                    R.sub.1       R.sub.2   X          m.p. (°C.)                          ______________________________________                                        SCH.sub.3     H         CH.sub.3                                              SOCH.sub.3    H         CH.sub.3                                              SO.sub.2 CH.sub.3                                                                           H         CH.sub.3   188-208°                            SC.sub.2 H.sub.5                                                                            H         CH.sub.3                                              SOC.sub.2 H.sub.5                                                                           H         CH.sub.3                                              SO.sub.2 C.sub.2 H.sub.5                                                                    H         CH.sub.3                                              S(CH.sub.2).sub.2 CH.sub.3                                                                  H         CH.sub.3                                              SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         CH.sub.3                                              SCH(CH.sub.3).sub.2                                                                         H         CH.sub.3                                              SOCH(CH.sub.3).sub.2                                                                        H         CH.sub.3                                              SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         CH.sub.3                                              S(CH.sub.2).sub.3 CH.sub.3                                                                  H         CH.sub.3                                              SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         CH.sub.3                                              SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         CH.sub.3                                              SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         CH.sub.3                                              SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         CH.sub.3                                              SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         CH.sub.3                                              SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         CH.sub.3                                              SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         CH.sub.3                                              SC(CH.sub.3).sub.3                                                                          H         CH.sub.3                                              SOC(CH.sub.3).sub.3                                                                         H         CH.sub.3                                              SO.sub.2 C(CH.sub.3).sub.3                                                                  H         CH.sub.3                                              SCH.sub.2 CHCH.sub.2                                                                        H         CH.sub.3                                              SOCH.sub.2 CHCH.sub.2                                                                       H         CH.sub.3                                              SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         CH.sub.3                                              SCH.sub.2 CHCHCH.sub.3                                                        SOCH.sub.2 CHCHCH.sub.3                                                                     H         CH.sub.3                                              SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         CH.sub.3                                               ##STR89##    H         CH.sub.3                                               ##STR90##    H         CH.sub.3                                               ##STR91##    H         CH.sub.3                                              SCH.sub.3     H         OCH.sub.3                                             SOCH.sub.3    H         OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                           H         OCH.sub.3                                             SC.sub.2 H.sub.5                                                                            H         OCH.sub.3                                             SOC.sub.2 H.sub.5                                                                           H         OCH.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                    H         OCH.sub.3  208-221°                            S(CH.sub.2).sub.2 CH.sub.3                                                                  H         OCH.sub.3  159-160°                            SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         OCH.sub.3  217-220°                            SCH(CH.sub.3).sub.2                                                                         H         OCH.sub.3                                             SOCH(CH.sub.3).sub.2                                                                        H         OCH.sub.3                                             SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         OCH.sub.3                                             S(CH.sub.2).sub.3 CH.sub.3                                                                  H         OCH.sub.3                                             SO(CH.sub.2).sub.3 CH.sub.3                                                   SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         OCH.sub.3                                             SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         OCH.sub.3                                             SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         OCH.sub.3                                             SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         OCH.sub.3                                             SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         OCH.sub.3                                             SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         OCH.sub.3                                             SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         OCH.sub.3                                             SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         OCH.sub.3                                             SC(CH.sub.3).sub.3                                                                          H         OCH.sub. 3                                            SOC(CH.sub.3).sub.3                                                                         H         OCH.sub.3                                             SO.sub.2 C(CH.sub.3).sub.3                                                                  H         OCH.sub.3                                             SCH.sub.2 CHCH.sub.2                                                                        H         OCH.sub.3                                             SOCH.sub.2 CHCH.sub.2                                                                       H         OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         OCH.sub.3                                             SCH.sub.2 CHCHCH.sub.3                                                                      H         OCH.sub.3                                             SOCH.sub.2 CHCHCH.sub.3                                                                     H         OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         OCH.sub.3                                              ##STR92##    H         OCH.sub.3                                              ##STR93##    H         OCH.sub.3                                              ##STR94##    H         OCH.sub.3                                             S(CH.sub.2).sub.3 CH.sub.3                                                                  H         C.sub.2 H.sub.5                                       SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         C.sub.2 H.sub.5                                       SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         C.sub.2 H.sub.5                                       SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         C.sub.2 H.sub.5                                       SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         C.sub.2 H.sub.5                                       SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         C.sub.2 H.sub.5                                       SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         C.sub.2 H.sub.5                                       SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         C.sub.2 H.sub.5                                       SC(CH.sub.3).sub.3                                                                          H         C.sub.2 H.sub.5                                       SOC(CH.sub.3).sub.3                                                                         H         C.sub.2 H.sub.5                                       SO.sub.2 C(CH.sub.3).sub.3                                                                  H         C.sub.2 H.sub.5                                       SCH.sub.2 CHCH.sub.2                                                                        H         C.sub.2 H.sub.5                                       SOCH.sub.2 CHCH.sub.2                                                                       H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         C.sub.2 H.sub.5                                       SCH.sub.2 CHCHCH.sub.3                                                                      H         C.sub.2 H.sub.5                                       SOCH.sub.2 CHCHCH.sub.3                                                                     H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         C.sub.2 H.sub.5                                        ##STR95##    H         C.sub.2 H.sub.5                                        ##STR96##    H         C.sub.2 H.sub.5                                        ##STR97##    H         C.sub.2 H.sub.5                                       SCH.sub.3     H         OC.sub.2 H.sub.5                                      SOCH.sub.3    H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.3                                                                           H         OC.sub.2 H.sub.5                                      SC.sub.2 H.sub.5                                                                            H         OC.sub.2 H.sub.5                                      SOC.sub.2 H.sub.5                                                                           H         OC.sub.2 H.sub.5                                      SO.sub.2 C.sub.2 H.sub.5                                                                    H         OC.sub.2 H.sub.5                                                                         175-178°                            S(CH.sub.2).sub.2 CH.sub.3                                                                  H         OC.sub.2 H.sub.5                                      SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         OC.sub.2 H.sub.5                                      SCH(CH.sub.3).sub.2                                                                         H         OC.sub.2 H.sub.5                                      SOCH(CH.sub.3).sub.2                                                                        H         OC.sub.2 H.sub.5                                      SO.sub.2 CH(Ch.sub.3).sub.2                                                                 H         OC.sub.2 H.sub.5                                      S(CH.sub.2).sub.3 CH.sub.3                                                                  H         OC.sub.2 H.sub.5                                      SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         OC.sub.2 H.sub.5                                      SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         OC.sub.2 H.sub.5                                      SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         OC.sub.2 H.sub.5                                      SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         OC.sub.2 H.sub.5                                      SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         OC.sub.2 H.sub.5                                      SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         OC.sub.2 H.sub.5                                      SC(CH.sub.3).sub.3                                                                          H         OC.sub.2 H.sub.5                                      SOC(CH.sub.3).sub.3                                                                         H         OC.sub.2 H.sub.5                                      SO.sub.2 C(CH.sub.3).sub.3                                                                  H         OC.sub.2 H.sub.5                                      SCH.sub.2 CHCH.sub.2                                                                        H         OC.sub.2 H.sub.5                                      SOCH.sub.2 CHCH.sub.2                                                                       H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         OC.sub.2 H.sub.5                                      SCH.sub.2 CHCHCH.sub.3                                                                      H         OC.sub.2 H.sub.5                                      SOCH.sub.2 CHCHCH.sub.3                                                                     H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         OC.sub.2 H.sub.5                                       ##STR98##    H         OC.sub.2 H.sub.5                                       ##STR99##    H         OC.sub.2 H.sub.5                                       ##STR100##   H         OC.sub.2 H.sub.5                                      S(CH.sub.2).sub.3 CH.sub.3                                                                  H         CH.sub.2 OCH.sub.3                                    SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         CH.sub.2 OCH.sub.3                                    SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         CH.sub.2 OCH.sub.3                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         CH.sub.2 OCH.sub.3                                    SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         CH.sub.2 OCH.sub.3                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         CH.sub.2 OCH.sub.3                                    SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         CH.sub.2 OCH.sub.3                                    SC(CH.sub.3).sub.3                                                                          H         CH.sub.2 OCH.sub.3                                    SOC(CH.sub.3).sub.3                                                                         H         CH.sub.2 OCH.sub.3                                    SO.sub.2 C(CH.sub.3).sub.3                                                                  H         CH.sub.2 OCH.sub.3                                    SCH.sub.2 CHCH.sub.2                                                                        H         CH.sub.2 OCH.sub.3                                    SOCH.sub.2 CHCH.sub.2                                                                       H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         CH.sub.2 OCH.sub.3                                    SCH.sub.2 CHCHCH.sub.3                                                                      H         CH.sub.2 OCH.sub.3                                    SOCH.sub.2 CHCHCH.sub.3                                                                     H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         CH.sub.2 OCH.sub.3                                     ##STR101##   H         CH.sub.2 OCH.sub.3                                     ##STR102##   H         CH.sub.2 OCH.sub.3                                     ##STR103##   H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.3                                                                           3-CH.sub.3                                                                              CH.sub.3                                              SO.sub.2 CH.sub.3                                                                           5-CF.sub.3                                                                              CH.sub.3                                              SO.sub.2 CH.sub.3                                                                           5-Cl      OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                           5-OCH.sub.3                                                                             OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                           5-NO.sub.2                                                                              OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.3                                                                           6-CH.sub.3                                                                              OCH.sub.3                                             SC.sub.2 H.sub.5                                                                            5-CH.sub.3                                                                              CH.sub.3                                              SOC.sub.2 H.sub.5                                                                           5-CF.sub.3                                                                              OCH.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                    5-Cl      OCH.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                    6-Br      OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          3-CH.sub.3                                                                              CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          3-Br      OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-CH.sub.3                                                                              OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-CF.sub.3                                                                              OC.sub.2 H.sub.5                                      SO.sub. 2 (CH.sub.2).sub.2 CH.sub.3                                                         5-OCH.sub.3                                                                             CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-Cl      OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          6-NO.sub.2                                                                              CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          6-CH.sub.3                                                                              OCH.sub.3                                             S(CH.sub.2).sub.3 CH.sub.3                                                                  5-CH.sub.3                                                                              OC.sub.2 H.sub.5                                      SO(CH.sub.2).sub.3 CH.sub.3                                                                 5-CF.sub.3                                                                              OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                3-Br      CH.sub.3                                              SO.sub.2 CH.sub.2 CHCH.sub.2                                                                3-Cl      OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                5-CH.sub.3                                                                              OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CHCH.sub.2                                                                5-OCH.sub.3                                                                             C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCH.sub.2                                                                5-CF.sub.3                                                                              C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCH.sub.2                                                                6-NO.sub.2                                                                              CH.sub.2 OCH.sub.3                                    SCH.sub.2 C(CH.sub.3)CH.sub.2                                                               5-CF.sub.3                                                                              OCH.sub.3                                              ##STR104##   3-CH.sub.3                                                                              OC.sub.2 H.sub.5                                       ##STR105##   5-Cl      CH.sub.2 OCH.sub.3                                    ______________________________________                                    

                  TABLE VI                                                        ______________________________________                                         ##STR106##                                                                   R.sub.1       R.sub.2   X          m.p. (°C.)                          ______________________________________                                        SCH.sub.3     H         CH.sub.3                                              SOCH.sub.3    H         CH.sub.3                                              SO.sub.2 CH.sub.3                                                                           H         CH.sub.3                                              SC.sub.2 H.sub.5                                                                            H         CH.sub.3                                              SOC.sub.2 H.sub.5                                                                           H         CH.sub.3                                              SO.sub.2 C.sub.2 H.sub.5                                                                    H         CH.sub.3                                              S(CH.sub.2).sub.2 CH.sub.3                                                                  H         CH.sub.3                                              SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         CH.sub.3                                              SCH(CH.sub.3).sub.2                                                                         H         CH.sub.3                                              SOCH(CH.sub.3).sub.2                                                                        H         CH.sub.3                                              SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         CH.sub.3                                              S(CH.sub.2).sub.3 CH.sub.3                                                                  H         CH.sub.3                                              SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         CH.sub.3                                              SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         CH.sub.3                                              SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         CH.sub.3                                              SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         CH.sub.3                                              SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         CH.sub.3                                              SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         CH.sub.3                                              SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         CH.sub.3                                              SC(CH.sub.3).sub.3                                                                          H         CH.sub.3                                              SOC(CH.sub.3).sub.3                                                                         H         CH.sub.3                                              SO.sub.2 C(CH.sub.3).sub.3                                                                  H         CH.sub.3                                              SCH.sub.2 CHCH.sub.2                                                                        H         CH.sub.3                                              SOCH.sub.2 CHCH.sub.2                                                                       H         CH.sub.3                                              SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         CH.sub.3                                              SCH.sub.2 CHCHCH.sub.3                                                                      H         CH.sub.3                                              SOCH.sub.2 CHCHCH.sub.3                                                                     H         CH.sub.3                                              SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         CH.sub.3                                               ##STR107##   H         CH.sub.3                                               ##STR108##   H         CH.sub.3                                               ##STR109##   H         CH.sub.3                                              SCH.sub.3     H         OCH.sub.3                                             SOCH.sub.3    H         OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                           H         OCH.sub.3                                             SC.sub.2 H.sub.5                                                                            H         OCH.sub.3                                             SOC.sub.2 H.sub.5                                                                           H         OCH.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                    H         OCH.sub.3  175-180°                            S(CH.sub.2).sub.2 CH.sub.3                                                                  H         OCH.sub.3                                             SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         OCH.sub.3                                             SCH(CH.sub.3).sub.2                                                                         H         OCH.sub.3                                             SOCH(CH.sub.3).sub.2                                                                        H         OCH.sub.3                                             SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         OCH.sub.3                                             S(CH.sub.2).sub.3 CH.sub.3                                                                  H         OCH.sub.3                                             SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         OCH.sub.3                                             SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         OCH.sub.3                                             SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         OCH.sub.3                                             SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         OCH.sub.3                                             SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         OCH.sub.3                                             SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         OCH.sub.3                                             SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         OCH.sub.3                                             SC(CH.sub.3).sub.3                                                                          H         OCH.sub.3                                             SOC(CH.sub.3).sub.3                                                                         H         OCH.sub.3                                             SO.sub.2 C(CH.sub.3).sub.3                                                                  H         OCH.sub.3                                             SCH.sub.2 CHCH.sub.2                                                                        H         OCH.sub.3                                             SOCH.sub.2 CHCH.sub.2                                                                       H         OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         OCH.sub.3                                             SCH.sub.2 CHCHCH.sub.3                                                                      H         OCH.sub.3                                             SOCH.sub.2 CHCHCH.sub.3                                                                     H         OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         OCH.sub.3                                              ##STR110##   H         OCH.sub.3                                              ##STR111##   H         OCH.sub.3                                              ##STR112##   H         OCH.sub.3                                             S(CH.sub.2).sub.3 CH.sub.3                                                                  H         C.sub.2 H.sub.5                                       SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         C.sub.2 H.sub.5                                       SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         C.sub.2 H.sub.5                                       SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         C.sub.2 H.sub.5                                       SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         C.sub.2 H.sub.5                                       SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         C.sub.2 H.sub. 5                                      SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         C.sub.2 H.sub.5                                       SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         C.sub.2 H.sub.5                                       SC(CH.sub.3).sub.3                                                                          H         C.sub.2 H.sub.5                                       SOC(CH.sub.3).sub.3                                                                         H         C.sub.2 H.sub.5                                       SO.sub.2 C(CH.sub.3).sub.3                                                                  H         C.sub.2 H.sub.5                                       SCH.sub.2 CHCH.sub.2                                                                        H         C.sub.2 H.sub.5                                       SOCH.sub.2 CHCH.sub.2                                                                       H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         C.sub.2 H.sub.5                                       SCH.sub.2 CHCHCH.sub.3                                                                      H         C.sub.2 H.sub.5                                       SOCH.sub.2 CHCHCH.sub.3                                                                     H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         C.sub.2 H.sub.5                                        ##STR113##   H         C.sub.2 H.sub.5                                        ##STR114##   H         C.sub.2 H.sub.5                                        ##STR115##   H         C.sub.2 H.sub.5                                       SCH.sub.3     H         OC.sub.2 H.sub.5                                      SOCH.sub.3    H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.3                                                                           H         OC.sub.2 H.sub.5                                      SC.sub.2 H.sub.5                                                                            H         OC.sub.2 H.sub.5                                      SOC.sub.2 H.sub.5                                                                           H         OC.sub.2 H.sub.5                                      SO.sub.2 C.sub.2 H.sub.5                                                                    H         OC.sub.2 H.sub.5                                      S(CH.sub.2).sub.2 CH.sub.3                                                                  H         OC.sub.2 H.sub.5                                      SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         OC.sub.2 H.sub.5                                      SCH(CH.sub.3).sub.2                                                                         H         OC.sub.2 H.sub.5                                      SOCH(CH.sub.3).sub.2                                                                        H         OC.sub.2 H.sub.5                                      SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         OC.sub.2 H.sub.5                                      S(CH.sub.2).sub.3 CH.sub.3                                                                  H         OC.sub.2 H.sub.5                                      SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         OC.sub.2 H.sub.5                                      SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         OC.sub.2 H.sub.5                                      SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         OC.sub.2 H.sub.5                                      SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         OC.sub.2 H.sub.5                                      SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         OC.sub.2 H.sub.5                                      SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         OC.sub.2 H.sub.5                                      SC(CH.sub.3).sub.3                                                                          H         OC.sub.2 H.sub.5                                      SOC(CH.sub.3).sub.3                                                                         H         OC.sub.2 H.sub.5                                      SO.sub.2 C(CH.sub.3).sub.3                                                                  H         OC.sub.2 H.sub.5                                      SCH.sub.2 CHCH.sub.2                                                                        H         OC.sub.2 H.sub.5                                      SOCH.sub.2 CHCH.sub.2                                                                       H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         OC.sub.2 H.sub.5                                      SCH.sub.2 CHCHCH.sub.3                                                                      H         OC.sub.2 H.sub.5                                      SOCH.sub.2 CHCHCH.sub.3                                                                     H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         OC.sub.2 H.sub.5                                       ##STR116##   H         OC.sub.2 H.sub.5                                       ##STR117##   H         OC.sub.2 H.sub.5                                       ##STR118##   H         OC.sub.2 H.sub.5                                      S(CH.sub.2).sub.3 CH.sub.3                                                                  H         CH.sub.2 OCH.sub.3                                    SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         CH.sub.2 OCH.sub.3                                    SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         CH.sub.2 OCH.sub.3                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         CH.sub.2 OCH.sub.3                                    SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         CH.sub.2 OCH.sub.3                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         CH.sub.2 OCH.sub.3                                    SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         CH.sub.2 OCH.sub.3                                    SC(CH.sub.3).sub.3                                                                          H         CH.sub.2 OCH.sub.3                                    SOC(CH.sub.3).sub.3                                                                         H         CH.sub.2 OCH.sub.3                                    SO.sub.2 C(CH.sub.3).sub.3                                                                  H         CH.sub.2 OCH.sub.3                                    SCH.sub.2 CHCH.sub.2                                                                        H         CH.sub.2 OCH.sub.3                                    SOCH.sub.2 CHCH.sub.2                                                                       H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         CH.sub.2 OCH.sub.3                                    SCH.sub.2 CHCHCH.sub.3                                                                      H         CH.sub.2 OCH.sub.3                                    SOCH.sub.2 CHCHCH.sub.3                                                                     H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         CH.sub.2 OCH.sub.3                                     ##STR119##   H         CH.sub.2 OCH.sub.3                                     ##STR120##   H         CH.sub.2 OCH.sub.3                                     ##STR121##   H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.3                                                                           3-CH.sub.3                                                                              CH.sub.3                                              SO.sub.2 CH.sub.3                                                                           5-CF.sub.3                                                                              CH.sub.3                                              SO.sub.2 CH.sub.3                                                                           5-Cl      OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                           5-OCH.sub.3                                                                             OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                           5-NO.sub.2                                                                              OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.3                                                                           6-CH.sub.3                                                                              OCH.sub.3                                             SC.sub.2 H.sub.5                                                                            5-CH.sub.3                                                                              CH.sub.3                                              SOC.sub.2 H.sub.5                                                                           5-CF.sub.3                                                                              OCH.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                    5-Cl      OCH.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                    6-Br      OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          3-CH.sub.3                                                                              CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          3-Br      OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-CH.sub.3                                                                              OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-CF.sub.3                                                                              OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-OCH.sub.3                                                                             CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-Cl      OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          6-NO.sub.2                                                                              CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          6-CH.sub.3                                                                              OCH.sub.3                                             S(CH.sub.2).sub.3 CH.sub.3                                                                  5-CH.sub.3                                                                              OC.sub.2 H.sub.5                                      SO(CH.sub.2).sub.3 CH.sub.3                                                                 5-CF.sub.3                                                                              OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                3-Br      CH.sub.3                                              SO.sub.2 CH.sub.2 CHCH.sub.2                                                                3-Cl      OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                5-CH.sub.3                                                                              OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CHCH.sub.2                                                                5-OCH.sub.3                                                                             C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCH.sub.2                                                                5-CF.sub.3                                                                              C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCH.sub.2                                                                6-NO.sub.2                                                                              CH.sub.2 OCH.sub.3                                    SCH.sub.2 C(CH.sub.3)CH.sub.2                                                               5-CF.sub.3                                                                              OCH.sub.3                                              ##STR122##   3-CH.sub.3                                                                              OC.sub.2 H.sub.5                                       ##STR123##   5-Cl      CH.sub.2 OCH.sub.3                                    ______________________________________                                    

                  TABLE VII                                                       ______________________________________                                         ##STR124##                                                                   R.sub.1       R.sub.2   X          m.p. (°C.)                          ______________________________________                                        SCH.sub.3     H         CH.sub.3                                              SOCH.sub.3    H         CH.sub.3                                              SO.sub.2 CH.sub.3                                                                           H         CH.sub.3                                              SC.sub.2 H.sub.5                                                                            H         CH.sub.3                                              SOC.sub.2 H.sub.5                                                                           H         CH.sub.3                                              SO.sub.2 C.sub.2 H.sub.5                                                                    H         CH.sub.3                                              S(CH.sub.2).sub.2 CH.sub.3                                                                  H         CH.sub.3                                              SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         CH.sub.3                                              SCH(CH.sub.3).sub.2                                                                         H         CH.sub.3                                              SOCH(CH.sub.3).sub.2                                                                        H         CH.sub.3                                              SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         CH.sub.3                                              S(CH.sub.2).sub.3 CH.sub.3                                                                  H         CH.sub.3                                              SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         CH.sub.3                                              SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         CH.sub.3                                              SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         CH.sub.3                                              SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         CH.sub.3                                              SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         CH.sub.3                                              SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         CH.sub.3                                              SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         CH.sub.3                                              SC(CH.sub.3).sub.3                                                                          H         CH.sub.3                                              SOC(CH.sub.3).sub.3                                                                         H         CH.sub.3                                              SO.sub.2 C(CH.sub.3).sub.3                                                                  H         CH.sub.3                                              SCH.sub.2 CHCH.sub.2                                                                        H         CH.sub.3                                              SOCH.sub.2 CHCH.sub.2                                                                       H         CH.sub.3                                              SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         CH.sub.3                                              SCH.sub.2 CHCHCH.sub.3                                                                      H         CH.sub.3                                              SOCH.sub.2 CHCHCH.sub.3                                                                     H         CH.sub.3                                              SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         CH.sub.3                                               ##STR125##   H         CH.sub.3                                               ##STR126##   H         CH.sub.3                                               ##STR127##   H         CH.sub.3                                              SCH.sub.3     H         OCH.sub.3                                             SOCH.sub.3    H         OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                           H         OCH.sub.3  205-240°                            SC.sub.2 H.sub.5                                                                            H         OCH.sub.3                                             SOC.sub.2 H.sub.5                                                                           H         OCH.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                    H         OCH.sub.3                                             S(CH.sub.2).sub.2 CH.sub.3                                                                  H         OCH.sub.3                                             SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         OCH.sub.3                                             SCH(CH.sub.3).sub.2                                                                         H         OCH.sub.3                                             SOCH(CH.sub.3).sub.2                                                                        H         OCH.sub.3                                             SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         OCH.sub.3                                             S(CH.sub.2).sub.3 CH.sub.3                                                                  H         OCH.sub.3                                             SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         OCH.sub.3                                             SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         OCH.sub.3                                             SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         OCH.sub.3                                             SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         OCH.sub.3                                             SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         OCH.sub.3                                             SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         OCH.sub.3                                             SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         OCH.sub.3                                             SC(CH.sub.3).sub.3                                                                          H         OCH.sub.3                                             SOC(CH.sub.3).sub.3                                                                         H         OCH.sub.3                                             SO.sub.2 C(CH.sub.3).sub.3                                                                  H         OCH.sub.3                                             SCH.sub.2 CHCH.sub.2                                                                        H         OCH.sub.3                                             SOCH.sub.2 CHCH.sub.2                                                                       H         OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         OCH.sub.3                                             SCH.sub.2 CHCHCH.sub.3                                                                      H         OCH.sub.3                                             SOCH.sub.2 CHCHCH.sub.3                                                                     H         OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         OCH.sub.3                                              ##STR128##   H         OCH.sub.3                                              ##STR129##   H         OCH.sub.3                                              ##STR130##   H         OCH.sub.3                                             S(CH.sub.2).sub.3 CH.sub.3                                                                  H         C.sub.2 H.sub.5                                       SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         C.sub.2 H.sub.5                                       SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         C.sub.2 H.sub.5                                       SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         C.sub.2 H.sub.5                                       SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         C.sub.2 H.sub.5                                       SCH(CH.sub.3)CH.sub. 2 CH.sub.3                                                             H         C.sub.2 H.sub.5                                       SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         C.sub.2 H.sub.5                                       SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         C.sub.2 H.sub.5                                       SC(CH.sub.3).sub.3                                                                          H         C.sub.2 H.sub.5                                       SOC(CH.sub.3).sub.3                                                                         H         C.sub.2 H.sub.5                                       SO.sub.2 C(CH.sub.3).sub.3                                                                  H         C.sub.2 H.sub.5                                       SCH.sub.2 CHCH.sub.2                                                                        H         C.sub.2 H.sub.5                                       SOCH.sub.2 CHCH.sub.2                                                                       H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         C.sub.2 H.sub.5                                       SCH.sub.2 CHCHCH.sub.3                                                                      H         C.sub.2 H.sub.5                                       SOCH.sub.2 CHCHCH.sub.3                                                                     H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         C.sub.2 H.sub.5                                        ##STR131##   H         C.sub.2 H.sub.5                                        ##STR132##   H         C.sub.2 H.sub.5                                        ##STR133##   H         C.sub.2 H.sub.5                                       SCH.sub.3     H         OC.sub.2 H.sub.5                                      SOCH.sub.3    H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.3                                                                           H         OC.sub.2 H.sub.5                                                                         210-214°                            SC.sub.2 H.sub.5                                                                            H         OC.sub.2 H.sub.5                                      SOC.sub.2 H.sub.5                                                                           H         OC.sub.2 H.sub.5                                      SO.sub.2 C.sub.2 H.sub.5                                                                    H         OC.sub.2 H.sub.5                                                                         163-167°                            S(CH.sub.2).sub.2 CH.sub.3                                                                  H         OC.sub.2 H.sub.5                                      SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         OC.sub.2 H.sub.5                                                                         168-171°                            SCH(CH.sub.3).sub.2                                                                         H         OC.sub.2 H.sub.5                                      SOCH(CH.sub.3).sub.2                                                                        H         OC.sub.2 H.sub.5                                      SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         OC.sub.2 H.sub.5                                      S(CH.sub.2).sub.3 CH.sub.3                                                                  H         OC.sub.2 H.sub.5                                      SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         OC.sub.2 H.sub.5                                      SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         OC.sub.2 H.sub.5                                      SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         OC.sub.2 H.sub.5                                      SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         OC.sub. 2 H.sub.5                                     SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         OC.sub.2 H.sub.5                                      SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         OC.sub.2 H.sub.5                                      SC(CH.sub.3).sub.3                                                                          H         OC.sub.2 H.sub.5                                      SOC(CH.sub.3).sub.3                                                                         H         OC.sub.2 H.sub.5                                      SO.sub.2 C(CH.sub.3).sub.3                                                                  H         OC.sub.2 H.sub.5                                      SCH.sub.2 CHCH.sub.2                                                                        H         OC.sub.2 H.sub.5                                      SOCH.sub.2 CHCH.sub.2                                                                       H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         OC.sub.2 H.sub.5                                      SCH.sub.2 CHCHCH.sub.3                                                                      H         OC.sub.2 H.sub.5                                      SOCH.sub.2 CHCHCH.sub.3                                                                     H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         OC.sub.2 H.sub.5                                       ##STR134##   H         OC.sub.2 H.sub.5                                       ##STR135##   H         OC.sub.2 H.sub.5                                       ##STR136##   H         OC.sub.2 H.sub.5                                      S(CH.sub.2).sub.3 CH.sub.3                                                                  H         CH.sub. 2 OCH.sub.3                                   SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         CH.sub.2 OCH.sub.3                                    SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         CH.sub.2 OCH.sub.3                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         CH.sub.2 OCH.sub.3                                    SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         CH.sub.2 OCH.sub.3                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         CH.sub.2 OCH.sub.3                                    SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         CH.sub.2 OCH.sub.3                                    SC(CH.sub.3).sub.3                                                                          H         CH.sub.2 OCH.sub.3                                    SOC(CH.sub.3).sub.3                                                                         H         CH.sub.2 OCH.sub.3                                    SO.sub.2 C(CH.sub.3).sub.3                                                                  H         CH.sub.2 OCH.sub.3                                    SCH.sub.2 CHCH.sub.2                                                                        H         CH.sub.2 OCH.sub.3                                    SOCH.sub.2 CHCH.sub.2                                                                       H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         CH.sub.2 OCH.sub.3                                    SCH.sub.2 CHCHCH.sub.3                                                                      H         CH.sub.2 OCH.sub.3                                    SOCH.sub.2 CHCHCH.sub.3                                                                     H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         CH.sub.2 OCH.sub.3                                     ##STR137##   H         CH.sub.2 OCH.sub.3                                     ##STR138##   H         CH.sub.2 OCH.sub.3                                     ##STR139##   H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.3                                                                           3-CH.sub.3                                                                              CH.sub.3                                              SO.sub.2 CH.sub.3                                                                           5-CF.sub.3                                                                              CH.sub.3                                              SO.sub.2 CH.sub.3                                                                           5-Cl      OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                           5-OCH.sub.3                                                                             OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                           5-NO.sub.2                                                                              OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.3                                                                           6-CH.sub.3                                                                              OCH.sub.3                                             SC.sub.2 H.sub.5                                                                            5-CH.sub.3                                                                              CH.sub.3                                              SOC.sub.2 H.sub.5                                                                           5-CF.sub.3                                                                              OCH.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                    5-Cl      OCH.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                    6-Br      OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          3-CH.sub.3                                                                              CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          3-Br      OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-CH.sub.3                                                                              OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-CF.sub.3                                                                              OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2 ).sub.2 CH.sub.3                                                         5-OCH.sub.3                                                                             CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-Cl      OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          6-NO.sub.2                                                                              CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          6-CH.sub.3                                                                              OCH.sub.3                                             S(CH.sub.2).sub.3 CH.sub.3                                                                  5-CH.sub.3                                                                              OC.sub.2 H.sub.5                                      SO(CH.sub.2).sub.3 CH.sub.3                                                                 5-CF.sub.3                                                                              OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                3-Br      CH.sub.3                                              SO.sub.2 CH.sub.2 CHCH.sub.2                                                                3-Cl      OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                5-CH.sub.3                                                                              OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CHCH.sub.2                                                                5-OCH.sub.3                                                                             C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCH.sub.2                                                                5-CF.sub.3                                                                              C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCH.sub.2                                                                6-NO.sub.2                                                                              CH.sub.2 OCH.sub.3                                    SCH.sub.2 C(CH.sub.3)CH.sub.2                                                               5-CF.sub.3                                                                              OCH.sub.3                                              ##STR140##   3-CH.sub.3                                                                              OC.sub.2 H.sub.5                                       ##STR141##   5-Cl      CH.sub.2 OCH.sub.3                                    ______________________________________                                    

                  TABLE VIII                                                      ______________________________________                                         ##STR142##                                                                   R.sub.1       R.sub.2   X          m.p. (°C.)                          ______________________________________                                        SCH.sub.3     H         CH.sub.3                                              SOCH.sub.3    H         CH.sub.3                                              SO.sub.2 CH.sub.3                                                                           H         CH.sub.3                                              SC.sub.2 H.sub.5                                                                            H         CH.sub.3                                              SOC.sub.2 H.sub.5                                                                           H         CH.sub.3                                              SO.sub.2 C.sub.2 H.sub.5                                                                    H         CH.sub.3                                              S(CH.sub.2).sub.2 CH.sub.3                                                                  H         CH.sub.3                                              SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         CH.sub.3                                              SCH(CH.sub.3).sub.2                                                                         H         CH.sub.3                                              SOCH(CH.sub.3).sub.2                                                                        H         CH.sub.3                                              SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         CH.sub.3                                              S(CH.sub.2).sub.3 CH.sub.3                                                                  H         CH.sub.3                                              SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         CH.sub.3                                              SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         CH.sub.3                                              SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         CH.sub.3                                              SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         CH.sub.3                                              SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         CH.sub.3                                              SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         CH.sub.3                                              SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         CH.sub.3                                              SC(CH.sub.3).sub.3                                                                          H         CH.sub.3                                              SOC(CH.sub.3).sub.3                                                                         H         CH.sub.3                                              SO.sub.2 C(CH.sub.3).sub.3                                                                  H         CH.sub.3                                              SCH.sub.2 CHCH.sub.2                                                                        H         CH.sub.3                                              SOCH.sub.2 CHCH.sub.2                                                                       H         CH.sub.3                                              SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         CH.sub.3                                              SCH.sub.2 CHCHCH.sub.3                                                                      H         CH.sub.3                                              SOCH.sub.2 CHCHCH.sub.3                                                                     H         CH.sub.3                                              SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         CH.sub.3                                               ##STR143##   H         CH.sub.3                                               ##STR144##   H         CH.sub.3                                               ##STR145##   H         CH.sub.3                                              SCH.sub.3     H         OCH.sub.3                                             SOCH.sub.3    H         OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                           H         OCH.sub.3  >255°                               SC.sub.2 H.sub.5                                                                            H         OCH.sub.3                                             SOC.sub.2 H.sub.5                                                                           H         OCH.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                    H         OCH.sub.3  >270°                               S(CH.sub.2).sub.2 CH.sub.3                                                                  H         OCH.sub.3                                             SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         OCH.sub.3                                             SCH(CH.sub.3).sub.2                                                                         H         OCH.sub.3                                             SOCH(CH.sub.3).sub.2                                                                        H         OCH.sub.3                                             SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         OCH.sub.3                                             S(CH.sub.2).sub.3 CH.sub.3                                                                  H         OCH.sub.3                                             SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         OCH.sub.3                                             SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         OCH.sub.3                                             SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         OCH.sub.3                                             SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         OCH.sub.3                                             SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         OCH.sub.3                                             SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         OCH.sub.3                                             SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         OCH.sub.3                                             SC(CH.sub.3).sub.3                                                                          H         OCH.sub.3                                             SOC(CH.sub.3).sub.3                                                                         H         OCH.sub.3                                             SO.sub.2 C(CH.sub.3).sub.3                                                                  H         OCH.sub.3                                             SCH.sub.2 CHCH.sub.2                                                                        H         OCH.sub.3                                             SOCH.sub.2 CHCH.sub.2                                                                       H         OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         OCH.sub.3                                             SCH.sub.2 CHCHCH.sub.3                                                                      H         OCH.sub.3                                             SOCH.sub.2 CHCHCH.sub.3                                                                     H         OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         OCH.sub.3                                              ##STR146##   H         OCH.sub.3                                              ##STR147##   H         OCH.sub.3                                              ##STR148##   H         OCH.sub.3                                             S(CH.sub.2).sub.3 CH.sub.3                                                                  H         C.sub.2 H.sub.5                                       SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         C.sub.2 H.sub.5                                       SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         C.sub.2 H.sub.5                                       SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         C.sub.2 H.sub.5                                       SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         C.sub.2 H.sub.5                                       SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         C.sub.2 H.sub.5                                       SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         C.sub.2 H.sub.5                                       SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         C.sub.2 H.sub.5                                       SC(CH.sub.3).sub.3                                                                          H         C.sub.2 H.sub.5                                       SOC(CH.sub.3).sub.3                                                                         H         C.sub.2 H.sub.5                                       SO.sub.2 C(CH.sub.3).sub.3                                                                  H         C.sub.2 H.sub.5                                       SCH.sub.2 CHCH.sub.2                                                                        H         C.sub.2 H.sub.5                                       SOCH.sub.2 CHCH.sub.2                                                                       H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         C.sub.2 H.sub.5                                       SCH.sub.2 CHCHCH.sub.3                                                                      H         C.sub.2 H.sub.5                                       SOCH.sub.2 CHCHCH.sub.3                                                                     H         C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         C.sub.2 H.sub.5                                        ##STR149##   H         OC.sub.2 H.sub.5                                       ##STR150##   H         OC.sub.2 H.sub.5                                       ##STR151##   H         OC.sub.2 H.sub.5                                      SCH.sub.3     H         OC.sub.2 H.sub.5                                      SOCH.sub.3    H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.3                                                                           H         OC.sub.2 H.sub.5                                      SC.sub.2 H.sub.5                                                                            H         OC.sub.2 H.sub.5                                      SOC.sub.2 H.sub.5                                                                           H         OC.sub.2 H.sub.5                                      SO.sub.2 C.sub.2 H.sub.5                                                                    H         OC.sub.2 H.sub.5                                                                         >270°                               S(CH.sub.2).sub.2 CH.sub.3                                                                  H         OC.sub.2 H.sub.5                                      SO(CH.sub.2).sub.2 CH.sub.3                                                                 H         OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          H         OC.sub.2 H.sub.5                                      SCH(CH.sub.3).sub.2                                                                         H         OC.sub.2 H.sub.5                                      SOCH(CH.sub.3).sub.2                                                                        H         OC.sub.2 H.sub.5                                      SO.sub.2 CH(CH.sub.3).sub.2                                                                 H         OC.sub.2 H.sub.5                                      S(CH.sub.2).sub.3 CH.sub.3                                                                  H         OC.sub.2 H.sub.5                                      SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         OC.sub.2 H.sub.5                                      SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         OC.sub.2 H.sub.5                                      SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         OC.sub.2 H.sub.5                                      SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         OC.sub.2 H.sub.5                                      SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         OC.sub.2 H.sub.5                                      SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         OC.sub.2 H.sub.5                                      SC(CH.sub.3).sub.3                                                                          H         OC.sub.2 H.sub.5                                      SOC(CH.sub.3).sub.3                                                                         H         OC.sub.2 H.sub.5                                      SO.sub.2 C(CH.sub.3).sub.3                                                                  H         OC.sub.2 H.sub.5                                      SCH.sub.2 CHCH.sub.2                                                                        H         OC.sub.2 H.sub.5                                      SOCH.sub.2 CHCH.sub.2                                                                       H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         OC.sub.2 H.sub.5                                      SCH.sub.2 CHCHCH.sub.3                                                                      H         OC.sub.2 H.sub.5                                      SOCH.sub.2 CHCHCH.sub.3                                                                     H         OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         OC.sub.2 H.sub.5                                       ##STR152##   H         OC.sub.2 H.sub.5                                       ##STR153##   H         OC.sub.2 H.sub.5                                       ##STR154##   H         OC.sub.2 H.sub.5                                      S(CH.sub.2).sub.3 CH.sub.3                                                                  H         CH.sub.2 OCH.sub.3                                    SO(CH.sub.2).sub.3 CH.sub.3                                                                 H         CH.sub.2 OCH.sub.3                                    SO.sub.2 (CH.sub.2).sub.3 CH.sub.3                                                          H         CH.sub.2 OCH.sub.3                                    SCH.sub.2 CH(CH.sub.3).sub.2                                                                H         CH.sub.2 OCH.sub.3                                    SOCH.sub.2 CH(CH.sub.3).sub.2                                                               H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.2 CH(CH.sub.3).sub.2                                                        H         CH.sub.2 OCH.sub.3                                    SCH(CH.sub.3)CH.sub.2 CH.sub.3                                                              H         CH.sub.2 OCH.sub.3                                    SOCH(CH.sub.3)CH.sub.2 CH.sub.3                                                             H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH(CH.sub.3)CH.sub.2 CH.sub.3                                                      H         CH.sub.2 OCH.sub.3                                    SC(CH.sub.3).sub.3                                                                          H         CH.sub.2 OCH.sub.3                                    SOC(CH.sub.3).sub.3                                                                         H         CH.sub.2 OCH.sub.3                                    SO.sub.2 C(CH.sub.3).sub.3                                                                  H         CH.sub.2 OCH.sub.3                                    SCH.sub.2 CHCH.sub.2                                                                        H         CH.sub.2 OCH.sub.3                                    SOCH.sub.2 CHCH.sub.2                                                                       H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.2 CHCH.sub.2                                                                H         CH.sub.2 OCH.sub.3                                    SCH.sub.2 CHCHCH.sub.3                                                                      H         CH.sub.2 OCH.sub.3                                    SOCH.sub.2 CHCHCH.sub.3                                                                     H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.2 CHCHCH.sub.3                                                              H         CH.sub.2 OCH.sub.3                                     ##STR155##   H         CH.sub.2 OCH.sub.3                                     ##STR156##   H         CH.sub.2 OCH.sub.3                                     ##STR157##   H         CH.sub.2 OCH.sub.3                                    SO.sub.2 CH.sub.3                                                                           3-CH.sub.3                                                                              CH.sub.3                                              SO.sub.2 CH.sub.3                                                                           5-CF.sub.3                                                                              CH.sub.3                                              SO.sub.2 CH.sub.3                                                                           5-Cl      OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                           5-OCH.sub.3                                                                             OCH.sub.3                                             SO.sub.2 CH.sub.3                                                                           5-NO.sub.2                                                                              OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.3                                                                           6-CH.sub.3                                                                              OCH.sub.3                                             SC.sub.2 H.sub.5                                                                            5-CH.sub.3                                                                              CH.sub.3                                              SOC.sub.2 H.sub.5                                                                           5-CF.sub.3                                                                              OCH.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                    5-Cl      OCH.sub.3                                             SO.sub.2 C.sub.2 H.sub.5                                                                    6-Br      OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          3-CH.sub.3                                                                              CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          3-Br      OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-CH.sub.3                                                                              OCH.sub. 3                                            SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-CF.sub.3                                                                              OC.sub.2 H.sub.5                                      SO.sub.2 (CH.sub.2).sub.2 CH.sub. 3                                                         5-OCH.sub.3                                                                             CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          5-Cl      OCH.sub.3                                             SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          6-NO.sub.2                                                                              CH.sub.3                                              SO.sub.2 (CH.sub.2).sub.2 CH.sub.3                                                          6-CH.sub.3                                                                              OCH.sub.3                                             S(CH.sub.2).sub.3 CH.sub.3                                                                  5-CH.sub.3                                                                              OC.sub.2 H.sub.5                                      SO(CH.sub.2).sub.3 CH.sub.3                                                                 5-CF.sub.3                                                                              OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                3-Br      CH.sub.3                                              SO.sub.2 CH.sub.2 CHCH.sub.2                                                                3-Cl      OCH.sub.3                                             SO.sub.2 CH.sub.2 CHCH.sub.2                                                                5-CH.sub.3                                                                              OC.sub.2 H.sub.5                                      SO.sub.2 CH.sub.2 CHCH.sub.2                                                                5-OCH.sub.3                                                                             C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCH.sub.2                                                                5-CF.sub.3                                                                              C.sub.2 H.sub.5                                       SO.sub.2 CH.sub.2 CHCH.sub.2                                                                6-NO.sub.2                                                                              CH.sub.2 OCH.sub.3                                    SCH.sub.2 C(CH.sub.3)CH.sub.2                                                               5-CF.sub.3                                                                              OCH.sub.3                                              ##STR158##   3-CH.sub.3                                                                              OC.sub.2 H.sub.5                                       ##STR159##   5-Cl      CH.sub.2 OCH.sub.3                                    ______________________________________                                    

Formulations

Useful formulations of the compounds of Formula I can be prepared inconventional ways. They include dusts, granules, pellets, solutions,suspensions, emulsions, wettable powders, emulsifiable concentrates andthe like. Many of these may be applied directly. Sprayable formulationscan be extended in suitable media and used at spray volumes of from afew liters to several hundred liters per hectare. High strengthcompositions are primarily used as intermediates for furtherformulation. The formulations, broadly, contain about 0.1% to 99% byweight of active ingredient(s) and at least one of (a) about 0.1% to 20%surfactant(s) and (b) about 1% to 99.9% solid or liquid diluent(s). Morespecifically, they will contain these ingredients in the followingapproximate proportions:

                  TABLE IX                                                        ______________________________________                                                    Active  Weight Percent*                                                       Ingredient                                                                            Diluent(s)                                                                              Surfactant(s)                                   ______________________________________                                        Wettable Powders                                                                            20-90      0-74     1-10                                        Oil Suspensions,                                                                             3-50     40-95     0-15                                        Emulsions, Solutions,                                                         (including Emulsifiable                                                       Concentrates)                                                                 Aqueous Suspension                                                                          10-50     40-84     1-20                                        Dusts          1-25     70-99     0-5                                         Granules and Pellets                                                                        0.1-95      5-99.9  0-15                                        High Strength 90-99      0-10     0-2                                         Compositions                                                                  ______________________________________                                         Active ingredient plus at least one of a Surfactant or a Diluent equals       100 weight percent.                                                      

Lower or higher levels of active ingredient can, or course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, N.J., but other solids, either mined or manufactured, may beused. The more absorptive diluents are preferred for wettable powdersand the denser ones for dusts. Typical liquid diluents and solvents aredescribed in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York,1950. Solubility under 0.1% is preferred for suspension concentrates;solution concentrates are preferably stable against phase separation at0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC PublishingCorp., Ridgewood, N.J., as well as Sisely and Wood, "Encylopedia ofSurface Active Agents", Chemical Publishing Co., Inc., New York, 1964,list surfactants and recommended uses. All formulations can containminor amounts of additives to reduce foaming, caking, corrosion,microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3,line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley & Sons, Inc.,New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 4 Wettable Powder

    ______________________________________                                        N--[(4-dimethylamino-6-methoxy-1,3,5-triazin-2-yl)-                                                       80%                                               aminocarbonyl]-2-(methylsulfonyl)benzenesulfonamide                           sodium alkylnaphthalenesulfonate                                                                          2%                                                sodium ligninsulfonate      2%                                                synthetic amorphous silica  3%                                                kaolinite                   13%                                               ______________________________________                                    

The ingredients are blended, hammer-milled until all the solids areessentially under 50 microns, reblended, and packaged.

EXAMPLE 5 Wettable Powder

    ______________________________________                                        N--[(4-chloro-6-ethoxypyrimidin-2-yl)aminocarbonyl]-                                                      50%                                               2-(propylsulfonyl)benzenesulfonamide                                          sodium alkylnaphthalenesulfonate                                                                           2%                                               low viscosity methyl cellulose                                                                             2%                                               diatomaceous earth          46%                                               ______________________________________                                    

The ingredients are blended, coarsely hammer-milled and then air-milledto produce particles essentially all below 10 microns in diameter. Theproduct is reblended before packaging.

EXAMPLE 6 Granule

    ______________________________________                                        Wettable Powder of Example 5                                                                          5%                                                    attapulgite granules   95%                                                    (U.S.S. 20-40 mesh; 0.84-0.42 mm)                                             ______________________________________                                    

A slurry of wettable powder containing ≈25% solids is sprayed on thesurface of attapulgite granules in a double-cone blender. The granulesare dried and packaged.

EXAMPLE 7 Extruded Pellet

    ______________________________________                                        N--[(4-dimethylamino-6-methoxy-1,3,5-triazin-2-yl)-                                                       25%                                               aminocarbonyl]-2-(propylsulfonyl)benzenesulfonamide                           anhydrous sodium sulfate    10%                                               crude calcium ligninsulfonate                                                                              5%                                               sodium alkylnaphthalenesulfonate                                                                           1%                                               calcium/magnesium bentonite 59%                                               ______________________________________                                    

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE 8 Oil Suspension

    ______________________________________                                        N--[(4-dimethylamino-6-methoxy-1,3,5-triazin-2-yl)-                                                       25%                                               aminocarbonyl]-2-(methylsulfonyl)benzenesulfonamide                           polyoxyethylene sorbitol hexaoleate                                                                        5%                                               highly aliphatic hydrocarbon oil                                                                          70%                                               ______________________________________                                    

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingthick suspension may be applied directly, but preferably after beingextended with oils or emulsified in water.

EXAMPLE 9 Wettable Powder

    ______________________________________                                        N--[(4-chloro-6-ethoxypyrimidin-2-yl)aminocarbonyl]-                                                      20%                                               2-(propylsulfonyl)benzenesulfonamide                                          sodium alkylnaphthalenesulfonate                                                                          4%                                                sodium ligninsulfonate      4%                                                low viscosity methyl cellulose                                                                            3%                                                attapulgite                 69%                                               ______________________________________                                    

The ingredients are thoroughly blended. After grinding in a hammer-millto produce particles essentially all below 100 microns, the material isreblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) andpackaged.

EXAMPLE 10 Low Strength Granule

    ______________________________________                                        N--[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbon-                                                       1%                                                 yl]-2-(propylsulfonyl)benzenesulfonamide                                      N,N--dimethylformamide     9%                                                 attapulgite granules       90%                                                (U.S.S. 20-40 sieve)                                                          ______________________________________                                    

The active ingredient is dissolved in the solvent and the solution issprayed upon dedusted granules in a double cone blender. After sprayingof the solution has been completed, the blender is allowed to run for ashort period and then the granules are packaged.

EXAMPLE 11 Aqueous Suspension

    ______________________________________                                        N--[(4-dimethylamino-6-methoxy-1,3,5-triazin-2-yl)-                                                        40%                                              aminocarbonyl]-2-(propylsulfonyl)benzenesulfonamide                           polyacrylic acid thickener  0.3%                                              dodecylphenol polyethylene glycol ether                                                                   0.5%                                              disodium phosphate            1%                                              monosodium phosphate        0.5%                                              polyvinyl alcohol           1.0%                                              water                       56.7%                                             ______________________________________                                    

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 12 Solution

    ______________________________________                                        N--[(4-dimethylamino-6-methoxy-1,3,5-triazin-2-yl)-                                                        5%                                               aminocarbonyl]-2-(methylsulfonyl)benzenesulfonamide                           water                       95%                                               ______________________________________                                    

The salt is added directly to the water with stirring to produce thesolution, which may then be packaged for use.

EXAMPLE 13 Low Strength Granule

    ______________________________________                                        N--[(4-chloro-6-ethoxypyrimidin-2-yl)aminocarbonyl]-                                                       0.1%                                             2-(propylsulfonyl)benzenesulfonamide                                          attapulgite granules        99.9%                                             (U.S.S. 20-40 mesh)                                                           ______________________________________                                    

The active ingredient is dissolved in a solvent and the solution issprayed upon dedusted granules in a double-cone blender. After sprayingof the solution has been completed, the material is warmed to evaporatethe solvent. The material is allowed to cool and then packaged.

EXAMPLE 14 Granule

    ______________________________________                                        N--[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-                                                      80%                                              2-(propylsulfonyl)benzenesulfonamide                                          wetting agent                 1%                                              crude ligninsulfonate salt (containing                                                                     10%                                              5-20% of the natural sugars)                                                  attapulgite clay              9%                                              ______________________________________                                    

The ingredients are blended and milled to pass through a 100 meshscreen. This material is then added to a fluid bed granulator, the airflow is adjusted to gently fluidize the material, and a fine spray ofwater is sprayed onto the fluidized material. The fluidization andspraying are continued until granules of the desired size range aremade. The spraying is stopped, but fluidization is continued, optionallywith heat, until the water content is reduced to the desired level,generally less than 1%. The material is then discharged, screened to thedesired size range, generally 14-100 mesh (1410-149 microns), andpackaged for use.

EXAMPLE 15 High Strength Concentrate

    ______________________________________                                        N--[(4-dimethylamino-6-methoxy-1,3,5-triazin-2-yl)-                                                        99%                                              aminocarbonyl]-2-(propylsulfonyl)benzenesulfonamide                           silica aerogel              0.5%                                              synthetic amorphous silica  0.5%                                              ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produce amaterial essentially all passing a U.S.S. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE 16 Wettable Powder

    ______________________________________                                        N--[(4-dimethylamino-6-methoxy-1,3,5-triazin-2-yl)-                                                        90%                                              aminocarbonyl]-2-(methylsulfonyl)benzenesulfonamide                           dioctyl sodium sulfosuccinate                                                                             0.1%                                              synthetic fine silica       9.9%                                              ______________________________________                                    

The ingredients are blended and ground in a hammer-mill to produceparticles essentially all below 100 microns. The material is siftedthrough a U.S.S. No. 50 screen and then packaged.

EXAMPLE 17 Wettable Powder

    ______________________________________                                        N--[(4-chloro-6-ethoxypyrimidin-2-yl)aminocarbonyl]-                                                      40%                                               2-(propylsulfonyl)benzenesulfonamide                                          sodium ligninsulfonate      20%                                               montmorillonite clay        40%                                               ______________________________________                                    

The ingredients are thoroughly blended, coarsely hammer-milled and thenair-milled to produce particles essentially all below 10 microns insize. The material is reblended and then packaged.

EXAMPLE 18 Oil Suspension

    ______________________________________                                        N--[(4-dimethylamino-6-methoxy-1,3,5-triazin-2-yl)-                                                       35%                                               aminocarbonyl]-2-(propylsulfonyl)benzenesulfonamide                           blend of polyalcohol carboxylic                                                                            6%                                               esters and oil soluble petroleum                                              sulfonates                                                                    xylene                      59%                                               ______________________________________                                    

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 5 microns. The product can beused directly, extended with oils, or emulsified in water.

EXAMPLE 19 Dust

    ______________________________________                                        N--[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-                                                      10%                                              2-(propylsulfonyl)benzenesulfonamide                                          attapulgite                  10%                                              Pyrophyllite                 80%                                              ______________________________________                                    

The active ingredient is blended with attapulgite and then passedthrough a hammer mill to produce particles substantially all below 200microns. The ground concentrate is then blended with powderedpyrophyllite until homogeneous.

EXAMPLE 20 Emulsifiable Concentrate

    ______________________________________                                        N--[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-                                                      20%                                              2-(propylsulfonyl)benzenesulfonamide                                          chlorobenzene                74%                                              sorbitan monostearate and polyoxyethylene                                                                   6%                                              condensates thereof                                                           ______________________________________                                    

The ingredients are combined and stirred to produce a solution which canbe emulsified in water for application.

Utility

The compounds of the present invention are active herbicides. They haveutility for broad-spectrum pre- and/or post-emergence weed control inareas where complete control of all vegetation is desired, such asaround fuel storage tanks, ammunition depots, industrial storage areas,parking lots, drive-in theaters, around billboards, highway and railroadstructures. Alternatively, the subject compounds are useful for theselective pre- or post-emergence weed control in crops, such as wheat,soybeans, cotton, corn and rape.

The rates of application for the compounds of the invention aredetermined by a number of factors, including their use as selective orgeneral herbicides, the crop species involved, the types of weeds to becontrolled, weather and climate, formulations selected, mode ofapplication, amount of foliage present, etc. In general terms, thesubject compounds should be applied at levels of around 0.02 to 5 kg/ha,the lower rates being suggested for use on lighter soils and/or thosehaving a low organic matter content, for selective weed control or forsituations where only short-term persistence is required.

The compounds of the invention may be used in combination with othercommercial herbicides examples of which are those of the triazine,triazole, uracil, urea, amide, diphenylether, carbamate and bipyridyliumtypes.

The herbicidal properties of the subject compounds were discovered in anumber of greenhouse tests. The test procedures and results follow.

TEST A

Seeds of crabgrass (Digitaria spp.), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia),morningglory (Ipomoea spp.), cocklebur (Xanthium pensylvanicum),sorghum, corn, soybean, sugar beet, rice, wheat and purple nutsedge(Cyperus rotundus) tubers were planted and treated pre-emergence withthe test chemicals dissolved in a non-phytotoxic solvent. At the sametime, these crop and weed species, along with cotton and bush bean, weretreated with a soil/foliage application. At the time of treatment, theplants ranged in height from 2 to 18 cm. Treated plants and controlswere maintained in a greenhouse for sixteen days, after which allspecies were compared to controls and visually rated for response totreatment. The ratings, summarized in Table A, are based on a numericalscale extending from 0=no injury, to 10=complete kill. The accompanyingdescriptive symbols have the following meanings:

C=chlorosis/necrosis,

E=emergence inhibition,

G=growth retardation,

H=formative effects,

U=unusual pigmentation,

X=axillary stimulation,

6Y=abscised buds or flowers.

The data indicate that the compounds tested are highly activeherbicides. Certain compounds from within the scope have utility forselective weed control in soybeans, wheat, cotton, corn and rape.##STR160##

    TABLE A      kg/ha g/ha Cmpd. 1 Cmpd. 2 Cmpd. 3 Cmpd. 4 Cmpd. 5 Cmpd. 6 Cmpd. 7     Cmpd. 8 Cmpd. 9 Cmpd. 10 Cmpd. 11 Cmpd. 12 Cmpd. 13 Cmpd. 14  Compound     15 .4 .05 .05 .05 .05 .05 .05 .05 50 50 50 50 50 50 50 400       POST-EMERGENCE Bush bean 9C 3C,9G 0 5C,9G,6Y 5C,9G,6Y 5C,9G,6Y     2C,8G,6Y 5C,9G,6Y -- -- -- -- 3C,9G,6Y 5C,9G,6Y 2C,2H 5C,9G,6Y  6Y     Cotton 6C,9G 2C,3H 0 3C,5G 3C,5H 4C,9G 2C,5G 2C,5G 4C,9G 3C,9H 2C,9G 2C     2C 3C,5G 4C,9G 5C,9G Morningglory 4C,9G 2C,8H 0 3C,8G 9C 5C,9G 0 5C,8G     4C,8H 3C,6H 1C,4G 5C,6H 3C,5G 3C,8G 1C,5H 3C,9G Cocklebur 9C 3G 0 2C,6H     9C 4C,9H 5H 5G 7G 1C 2C,6H 4C,8H 0 2C,6H 2C 2C,5G Sicklepod 9C 3C 0     2C,7H 4C,9G 3C,5G 2C 1C 2C,3H 0 3C,9G 2C,2H 1C 2C,7H 2C 2C,4G Nutsedge     8G 0 0 2C 2G 3C,9G 0 3G 4G 2C,8G 2C,6G 0 3C,9G 2C 0 0 Crabgrass 9C 1C,5G     0 2C,9G 1C,5G 1C,3G 2G 0 2C,8G 2C,7G 2C,7G 2C,2G 2C,5G 2C,9G 5H 4C,8G     Barnyardgrass 9C 2C,9H 0 4C,9H 2C,9H 2C,6H 2C,6H 2C,6H 9H 2C,9H 3C,9H     3C,8H 5C,9H 4C,9H 5C,9H 10C Wild Oats 9C 2C 0 4C,8H 2C,9G 0 0 0 3C,9H     2C,9G 2C,8G 8G 0 4C,8H 4C,9H 9C Wheat 9C 2C 0 3C,9G 2C,9G 0 0 0 9C 5C,9G     8G 3G 0 3C,9G 2C,8G 5C,9G Corn 7U,9C 2C,8H 0 2U,9G 2U,9G 2G 2C,5G 1C,4G     3U,9G 4G 3C,9H 2C,7H 1C,4G 2U,9G 2C,7H 5U,9H Soybean 9C 2C,3H 0 2C,8H,5X     6C,9G 1C,3G 4G 0 2C,8G 3C,8G 2C,7H 2C,7H 5G 2C,8H,5X 3H,7G 3H,9G Rice     6C,9G 3C,9G 0 5C,9G 6C,9G 6G 5G 8G 4C,9G 9G 4C,9G 4C,9G 3C,9G 5C,9G     2C,9G 6C,9G Sorghum 5U,9G 9G 0 3C,9G 2C,9G 9G 2C,7H 2C,8H 2U,9G 1U,9G     2C,9H 3C,9H 3C,9H 3C,9G 3U,9G 4U,9C Sugar beet -- -- -- -- 3C,8H 3C,7G     4G 0 10C 2C,4H 2C,7G 3C,7H 2G --  -- -- PRE-EMERGENCE Morningglory 9G 0     0 2C,8G 9G 8H 2C,7H 5C,9G 8H 8G 8G 2C,2H 9G 2C,8G 9G 9H Cocklebur 9H 0 0     2C,7G -- 9H 9H 9H 9H 9H 9H 8G 9H 2C,7G -- 9H Sicklepod 2C,9G 0 0 3C 7H     5G 9G 0 5G 5G 7H -- 0 3C 1C 6G Nutsedge 2C,7G 0 0 1C 0 5G 10E 2G 3G 0 5G     5G 5C,9G 1C 1C,4G 2C,8G Crabgrass 7C,9G 2C 0 5C,9G 0 1C 2C 0 4G 2G 6G 0     2G 5C,9G 1C 2C,8G Barnyardgrass 7C,9H 2C,8H 0 3C,9H 9H 2C,5H 4C,7H 5G     3C,8H 3C,7H 4C,9H 2C,6G 2C,6H 3C,9H 3C,9H 3C,9H Wild Oats 5C,9G 1C,3G 0     5C,9G 2C,8G 3G 2C 0 9G 3C,8H 4C,8G 2C,6G 2G 5C,9G 2C,8G 3C,9H Wheat     4C,9G 4G 0 3C,9G 9G 3G 0 3G 2C,9G 2C,8G 4C,9G 2G 6G 3C,9G 2C,7G 2C,9G     Corn 3C,9G 2C,7G 0 2C,9G 2C,9G 6G 2C,5G 6G 9G 5G 2C,9G 2C,6G 5G 2C,9G     3C,7G 2C,9G Soybean 8G 0 0 3C,3G 0 0 0 1C 0 2G 1C,5G 1H 0 3C,3G 0 2C,8H     Rice 10E 2C,8G 0 9H 5C,9H 2C,8H 4C,7G 3C,7G 10E 3C,9H 5C,9H 2C,7H 3C,8H     9H 10E 10E Sorghum 6C,9H 2C,9G 0 2C,9H 2C,9H 2C,9H 2C,9H 2C,7H 2C,9H     3C,9H 4C,9H 2C,9G 2G 2C,9H 2C,9G 2C,9G Sugar beet -- -- -- -- 10E 5C,9G     9G 8G 9C 7G 2C,9G 9H 8G -- -- -- Cotton         9G 7G 8G 1C -- -- --     --    kg/ha Cmpd. 16 Cmpd. 17 Cmpd. 18 Cmpd. 19 Cmpd. 20 Cmpd. 21 Cmpd.     22 Compound 23 Compound 24 Compound 25 Compound 26  Compound 27 Compound     28 0.05 0.05 0.05 0.05 0.05 0.05 0.05 0.4 0.05 0.4 0.05 0.4 0.05 0.4     0.05 0.4 0.05 0.4 0.05       POST-EMERGENCE Bush bean 3C,8H,6Y 5C,6G,6Y 1H 2C,2H -- -- -- -- -- --     -- -- -- -- -- -- -- -- -- Cotton 2C,2G 2C 5C,8H 2C,3H,7G 0 4C,8G 2G     3C,3H 3C,3G 3C,7G 2C,3G 4C,9H 4C,8H 10C 3C,5G 10C 4C,8H 5G 1C Morningglor     y 2C 2C 2C,8H 3C,8H 1C 2C,3G 2G 3C,5H 3C,5H 2C,5H 5H,4C 9C 4C,9G 2C,7G     2C 9C 3C 4C,6H 2C,2G Cocklebur 2C,8H 5G 2C,2H 1H 0 3H 7G 1H 0 1H 0 5G 3G     3G 2G 1C,3G 0 1C 0 Sicklepod 2C 2C,5G 2C,7H 3C,4H 1C 2C,4H 2G 1C,3G 1C     1H 1C 3C,8H 4C,7H 3C,6H 2C,4G 4C,8G 0 3C,3H 0 Nutsedge 0 0 2C 0 0 2C,7G     0 0 0 5G 2G 5G 0 2C,8G 2G 2G 0 0 0 Crabgrass 4G 2C,6G 2C,7G 2C,4G 0     2C,8G 2C,7G 5G 5G,2C 1C,3G 0 3C,8G 2C,5G 3C,9G 3C,8G 3C,9G 7G 2C,5G 1C     Barnyardgrass 2C,5H 3C,8H 3C,9H 2C,4H 2H 3C,9H 4C,9H 3C,8H 3C,7H 0 0     3C,9H 2C,9H 5C,9H 4C,9H 5C,9H 2C,5G 3C,8H 2C,3H Wild Oats 2C,8G 2C 3C,8G     0 0 2C,8G 2C,3G 2C,8G 2C,8G 3C,5G 0 2C,9G 9G 5C,9G 2C,9G 9C 3C,9G 2C,7G     2C,5G Wheat 2G 1C 2C,4G 0 0 9G 4G 7G 7G 0 0 2C,9G 3C,8G 2C,9G 9C 10C     2C,9G 7G 2G Corn 2H 1C,3G 2C,8H 1C,2H 0 3C,9H 3C,5H 2C,9H 3C,8H 5C,6H     2C,5H 3U,9G 1U,8G 3C,9G 3C,9G 10C 2U,9G 3C,8H 2C,3H Soybean 2C,3G 1C,3G     2C,5H 1C,2G 2G 2C,3H 1H 3C,6H 1C,2G 3C,3H 2C,3G 2C,8G 3C,5H 3C,9G 3C,5G     5C,9G 2C,3H 3C,8G 2H,4G Rice 4C,9G 3C,9G 4C,9G 3C,9G 3G 5C,9G 2C,8G     5C,9G 5C,9G 3C,8G 2C,5G 3C,9G 5C,9G 5C,9G 5C,9G 5C,9G 6C,9G 4C,8G 3C,7G     Sorghum 3C,9G 3C,9H 2C,9H 3C,9H 2G 4C,9H 4C,9H 2C,9H 4C,9H 3C,9G 3C,9H     2U,9G 9G 3C,9G 3C,9H 6C,9G 9G 2C,2H 2G Sugar beet 2C,3G 2C,5G 0 9C 0     3C,5H 3C,6G 3C,5H 4C,4H 1C 3C,3H 9C 3C,7G 5C,9G 3C,8G 3C,7G 2C,6H 2C,6G     1C PRE-EMERGENCE Morningglory 2C 3C,5G 9G 9G 1C 2C,5G 3H 2C,3H 6H 8H     2C,7H 9C 9H 9G 2C 9C 9G 2C 2G Cocklebur 1H 9H 9H 9H 0 9H 8H 0 0 7H 2G 9H     8H 8H 9H 9H 3H 0 0 Sicklepod 3H 2C,3G 2C,5G 3C,3H 1C 2C,8G 3C 1C 0 5C,8G     0 3C,9G 3C,3H 8G 5G 9C -- -- 0 Nutsedge 0 5G 0 0 0 0 3G 0 0 2G 0 3G 0 5G     3G 8G 0 0 0 Crabgrass 2G 5G,2C 3C,6G 2C 0 2C,5G 5G 3G 2G 2C,3G 0 5G 2G     5C,9G 3C,9G 5C,9G 0 2G 0 Barnyardgrass 2C,8H 3C,9H 9H 3C,6G 0 3C,9H     4C,9H 2H 2G 3G,5C 0 3C,9H 3C,7H 5C,9G 3C,7H 5C,9H 1C 3C,6G 0 Wild Oats     2C,8H 3C,9G 5C,9H 2C,6G 0 4C,9G 4C,8G 2C 2C,4G 3C,9G 2G 3C,9H 3C,8G     6C,9G 4C,9H 6C,9H 3C,8H 3C,7G 1H Wheat 5G 2C,9G 9H 6G 0 2C,9G 2C,9G 3G     6G 3C,9G 0 5C,9H 3C,8G 6C,9H 5C,9H 7C,9H 2C,9H 3C,9G 1H Corn 4G 2C,9H 9G     3C,8H 0 2C,9H 3C,8H 3C,8H 3C,8H 3C,9H 4C,7G 9G 8G 6C,9H 4C,9H 7C,9H     2C,8G 3C,8G 2C Soybean 0 0 2C,2H 1C 1C 2C,2H 0 2C 1C 3C,4H 1C 3H 1H     3C,4H 1G 1C,3G 0 2C,2H 0 Rice 2C,8H 3C,7H 10E 5C,9H 2C 10H 5C,9H 2C,8G     3C,8H 4C,9H 5G 10E 5C,9H 10E 10E 10E 10E 5C,9H 2C Sorghum 3C,8H 3C,9H     5C,9H 1C,9G 2C,4G 4C,9H 4C,9H 3C,8H 3C,8H 3C,9H 2C,8G 5C,9H 3C,9G 5C,9H     5C,9H 5C,9H 3C,9G 4C,9G 2C Sugar beet 3C,8G 9G 8G 2C,9G 6G 9C 9G 0 0     4C,8H 1C 9C 2C,7G 10C 4C,9G 2C,8G 2C,8G 0 2H Cotton --  -- -- -- -- 8G 0     2G 0 3C,3H 1C 9G 6G,2C 3C,9G 9G 9G 2C,7G 2G 3G

TEST B

Two plastic bulb pans were filled with fertilized and limed Woodstownsandy loam. One pan was planted with corn, sorghum, Kentucky bluegrassand several grass weeds. The other pan was planted with cotton,soybeans, purple nutsedge (Cyperus rotundus), and several broadleafweeds. The following grass and broadleaf weeds were planted: crabgrass(Digitaria sanguinalis), barnyardgrass (Echinochloa crusgalli), wildoats (Avena fatua), johnsongrass (Sorghum halepense), dallisgrass(Paspalum dilatatum), giant foxtail (Setaria faberii), cheatgrass(Bromus secalinus), mustard (Brassica arvensis), cocklebur (Xanthiumpensylvanicum), pigweed (Amaranthus retroflexus), morningglory (Ipomoeahederacea), sicklepod (Cassia obtusifolia), teaweed (Sida spinosa),velvetleaf (Abutilon theophrasti), and jimsonweed (Datura stramonium). A12.5 cm diameter plastic pot was also filled with prepared soil andplanted with rice and wheat. Another 12.5 cm pot was planted with sugarbeets. The above four containers were treated preemergence with severaltest compounds within the scope of the invention.

Twenty-eight days after treatment, the plants were evaluated andvisually rated for response to the chemical treatments utilizing therating system described previously for Test A. The data are summarizedin Table B.

                                      TABLE B                                     __________________________________________________________________________    PRE-EMERGENCE ON WOODSTOWN SANDY LOAM                                                 Compound No.                                                                  1           5             4       6                                   kg/ha   .015                                                                              .060                                                                              .250                                                                              .015                                                                             .030                                                                             .120                                                                              .250                                                                              .030                                                                              .120                                                                              .030                                                                              .120                            __________________________________________________________________________    Crabgrass                                                                             7G  8G,3H                                                                             9G,9C                                                                             0  0  6G  7G  4G  8G,5H                                                                             0   0                               Barnyardgrass                                                                         4G,3C                                                                             6G  9G,9C                                                                             3G 3G 7G  8G  2G  5G,2H                                                                             5G  7G                              Sorghum 7G,5H                                                                             10C 10C 5G 7G 9G  10C --  --  7G  9G                              Wild Oats                                                                             2G  7G,5H                                                                             7G,5H                                                                             3G 4G 8G  9G  0   5G  2G  6G                              Johnsongrass                                                                          5G,3H                                                                             9G,8C                                                                             9G,9C                                                                             5G 6G 8G  9G  4G  6G,5H                                                                             4G  8G                              Dallisgrass                                                                           3G  5G  7G  0  6G 6G  8G  5G  8G,3H                                                                             2G  7G                              Giant Foxtail                                                                         4G  8G,3H                                                                             10C 2G 3G 8G  9G  3G  8G,5H                                                                             5G  7G                              Ky. Bluegrass                                                                         --  9G,9C                                                                             10E 7G 8G 9G  9G,9C                                                                             7G,3H                                                                             9G,8C                                                                             3G  8G                              Cheatgrass                                                                            10E 10C 10E 5G 7G 9G  9G  0   6G  7G  9G                              Sugar beets                                                                           5G,3C                                                                             8G,8C                                                                             10E 3G 7G 9G  10C 3G  5G,2H                                                                             7G  10C                             Corn    3G  7G,5H                                                                             9G,9C                                                                             0  0  5G,3H                                                                             8G,7H                                                                             0   7G,5H                                                                             3G  4G,2C                           Mustard 5G  8G,8C                                                                             10C 6G 6G 9G  9G  6G,3H                                                                             9G,5H                                                                             9G  9G                              Cocklebur                                                                             4G  4G  6G,5H                                                                             3G 7G 7G  9G  0   3G  6G  8G                              Pigweed --  10E 10E -- -- --  --  10C 10C --  --                              Nutsedge                                                                              0   2G  7G  0  0  2G  5G  0   0   7G  9G                              Cotton  0   3G  7G,5H                                                                             4G 4G 5G  7G  0   0   2G,2C                                                                             2G,2C                           Morningglory                                                                          0   8G,7C                                                                             8G,5C                                                                             0  2G 3G  8G  0   3G  5G,3C                                                                             5G,5C                           Sicklepod                                                                             0   7G  8G,5C                                                                             0  0  2G  8G  3G  4G  0   2G                              Teaweed 0   0   7G,3H                                                                             0  2G 7G  8G  0   0   0   0                               Velvetleaf                                                                            0   5G,2H                                                                             7G,5H                                                                             0  0  5G  7G  0   3G  7G  8G                              Jimsonweed                                                                            2G  6G  7G  0  3G 7G  9G  0   3G  7G  9G                              Soybean 0   3G,2H                                                                             6G,5H                                                                             2G 3G 5G,5H                                                                             6G,5H                                                                             0   0   0   2G                              Rice    10C 8G,8C                                                                             10E 6G 7G 8G  10C 6G,3H                                                                             8G,9C                                                                             7G  8G                              Wheat   3G  8G,5H                                                                             10C 2G 3G 6G  8G  0   7G,5C                                                                             2G  2G                              __________________________________________________________________________

TEST C

The test chemicals, dissolved in a non-phytotoxic solvent, were appliedin an overall spray to the foliage and surrounding soil of selectedplant species. One day after treatment, plants were checked for rapidburn injury. Approximately fourteen days after treatment all specieswere visually compared to untreated controls and rated for response totreatment. The rating system was as described previously for Test A. Thedata are presented in Table C.

All plant species were seeded in Woodstown sandy loam soil and grown ina greenhouse. The following species were grown in soil contained inplastic pots (25 cm diameter by 13 cm deep): soybeans, cotton, alfalfa,corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania(Sesbania exaltata), sicklepod (Cassia obtusifolia), morningglory(Ipomoea hederacea), jimsonweed (Datura stramonium), cockelbur (Xanthiumpensylvanicum), crabgrass (Digitaria spp.), nutsedge (Cyperus rotundus),barnyardgrass (Echinochloa crusgalli), giant foxtail (Setaria faberii),and wild oats (Avena fatua). The following species were grown in soil ina paper cup (12 cm diameter by 13 cm deep): sunflower, sugar beets andmustard. All plants were sprayed approximately 14 days after planting.Additional plant species are sometimes added to this standard test inorder to evaluate unusual selectivity.

                  TABLE C                                                         ______________________________________                                        Over-the-Top Soil/Foliage Treatment                                                                Compound 1                                               Rate kg/ha           0.015                                                    ______________________________________                                        Soybeans             9G,4C                                                    Velvetleaf           4G                                                       Sesbania             9G                                                       Sicklepod            8G                                                       Cotton               9G                                                       Morningglory         7G,4C                                                    Alfalfa              3G                                                       Jimsonweed           6G                                                       Cocklebur            4G                                                       Corn                 9G,8C                                                    Crabgrass            9G                                                       Rice                 9G,7C                                                    Nutsedge             0                                                        Barnyardgrass        3G                                                       Wheat                8G,4C                                                    Giant Foxtail        10C                                                      Wild Oats            8G                                                       Sorghum              8G,2U                                                    Bindweed             0                                                        Johnsongrass         10C                                                      Sunflower            7G,1H                                                    Rape                 0                                                        Sugar beets          4G                                                       ______________________________________                                    

What is claimed is:
 1. A compound of the formula ##STR161## wherein R₁is S(O)_(n) R₃ ;R₂ is H, F, Cl, Br, CH₃, OCH₃, CF₃ or NO₂ ; R₃ is C₁ -C₄alkyl, C₃ -C₄ alkenyl or cyclopropylmethyl; n is 0, 1 or 2; X is CH₃, C₂H₅, CH₃ O, C₂ H₅ O, CH₂ OCH₃ or Cl; Y is Cl, F, Br, NH₂, NHCH₃ orN(CH₃)₂ ; and Z is CH;and their agriculturally suitable salts; providedthat (1) when R₃ is C₃ -C₄ alkenyl, then Y is NH₂, NHCH₃ or N(CH₃)₂ ;(2) when R₃ is C₁ -C₂ alkyl and Y is Cl or Br, then X is other than CH₃or OCH₃ ; (3) when R₃ is C₁ -C₂ alkyl and Y is NH₂ or NHCH₃, then X isother than Cl, CH₂ CH₃ or CH₂ OCH₃ ; (4) when Y is Cl, F or Br, then Xis CH₃, OCH₃ or OCH₂ CH₃ ; and (5) when X is Cl, then Y is N(CH₃)₂. 2.Compounds of claim 1 where n is
 2. 3. Compounds of claim 2 wherein R₂ isH, Cl, CH₃, CH₃ O or CF₃.
 4. Compounds of claim 3 where X is CH₃ orOCH₃.
 5. Compounds of claim 4 where R₂ is H.
 6. The compound of claim 1which isN-[(4-chloro-6-ethoxypyrimidin-2-yl)aminocarbonyl]-2-(propylsulfonyl)benzenesulfonamide.7. The compound of claim 1 which isN-[(4-chloro-6-methoxypyrimidin-2-yl)aminocarbonyl]-2-(propylsulfonyl)benzenesulfonamide.8. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 1and at least one of the following: surfactant, solid or liquid diluent.9. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 2and at least one of the following: surfactant, solid or liquid diluent.10. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 3and at least one of the following: surfactant, solid or liquid diluent.11. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 4and at least one of the following: surfactant, solid or liquid diluent.12. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 5and at least one of the following: surfactant, solid or liquid diluent.13. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of the compound of claim6 and at least one of the following: surfactant, solid or liquiddiluent.
 14. A method for controlling the growth of undesired vegetationwhich comprises applying to the locus to be protected an effectiveamount of a compound of claim
 1. 15. A method for controlling the growthof undesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 2. 16. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim3.
 17. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 4. 18. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 5. 19. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of the compound ofclaim 6.